| 1. |
L. Antypenko, O. Antypenko, I. Kamaukh, O. Rebets, S. Kovalenko, M. Arisawa , 5,6-Dihydrotetrazolo[1,5-c]quinazolines: Toxicity Prediction, Synthesis, Antimicrobial Activity, Molecular Docking and Perspectives, Arch. Pharm, in press (2023)., 2023.06. |
| 2. |
T. Kaneko, Y. Mita, K. Nozawa-Kumada, M. Yazaki, M. Arisawa, E. Niki, N. Noguchi, Y. Saito, Antioxidant Action of Persulfides and Polysulfides Against Free Radical-Mediated Lipid Peroxidation, Free Radical Research, 1-14., 2023.01. |
| 3. |
Y. Wang, R. Segawa, Y. Weng, K. Nakai, K. Ohashi, M. Hiratsuka, M. Arisawa, N. Hirasawa , Selective Induction of Thymic Stromal Lymphopoietin Expression by Novel Nitrogen-Containing Steroid Compounds in PAM-212 Cells, J. Transl. Autoimmun., 6, 100186, (2023)., 2023.06. |
| 4. |
S. Zhang, M. Bao, M. Arisawa, M. Yamaguchi , Stable and Unstable Concentration Oscillations Induced by Temperature Oscillations on Reversible Noneequilibrium Chemical Reactions of Helicene Oligomers, Int. J. Mol. Sci., 24, 693, (2023)., 2023.06. |
| 5. |
K. Fukumoto, M. Yazaki, M. Arisawa, Rhodium-Catalyzed Synthesis of Peptide Polysulfides by Insertion of Sulfur into Unprotected Peptide Disulfides, Organic Letters 24(44) 8176-8179, DOI: 10.1021/acs.orglett.2c03257, 24(44), (44), 8176-8179, 2022.11. |
| 6. |
K. Fukumoto, M. Yazaki, M. Arisawa, Rhodium-Catalyzed Insertion Reaction of Perfluoroarenes into Unprotected Peptide Disulfides, Asian J. Org. Chem., 11, e202200340, (2022)., 11, 9, e202200340-e202200340, 2022.09. |
| 7. |
M. Arisawa, Development of Biostimulants and Pharmaceuticals Using Synthetic Heavy-Heteroatom Organic Compounds, Journal of the Society of Japanese Women Scientists, 22, 69-79 (2022).
, DOI:10.5939/sjws.220014 , 22, 69-79, 2022.01. |
| 8. |
Mieko Arisawa, Taro Mizuno, Kanako Nozawa-Kumada, Kaori Itto-Nakama, Miyu Furuta, Saori Tanii, Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl)ureas Involving an Equilibrium Shift, Organic Letters, 23, 9382-9386, 2021.12. |
| 9. |
Mieko Arisawa, Taro Mizuno, Kanako Nozawa-Kumada, Kaori Itto-Nakama, Miyu Furuta, Saori Tanii, Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl)ureas Involving an Equilibrium Shift, Organic Letters, in press, 2021.12. |
| 10. |
M. Arisawa, M. Yamaguchi, Thiiranes and Thiirenes–Fused Ring Derivatives, Comprehensive Heterocyclic Chemistry IV, 1, 413-435, 2021.12. |
| 11. |
Mieko Arisawa, Miyu Yoshida, Kohei Fukumoto, Tsukasa Sawato, Masahiko Yamaguchi, Masaki Matsubara, Kiyoshi Kanie, Three-state Structural Switching and Selective Molecular Interactions of Cylindrical Concentric Monodomain Liquid Crystal Elastomer, ChemistrySelect, 6, 12604-12609, 2021.11. |
| 12. |
Mieko Arisawa, Miyu Yoshida, Kohei Fukumoto, Tsukasa Sawato, Masahiko Yamaguchi, Masaki Matsubara, Kiyoshi Kanie, Three-state Structural Switching and Selective Molecular Interactions of Cylindrical Concentric Monodomain Liquid Crystal Elastomer, ChemistrySelect, 6, 12604-12609, 2021.11. |
| 13. |
Unstable and Stable Thermal Hysteresis Under Thermal Triangle Waves. |
| 14. |
Rhodium-Catalyzed Oxidation of Unprotected Peptide Thiols to Disulfides with Oxygen in Water. |
| 15. |
Rhodium-Catalyzed Synthesis of Organosulfur Compounds Involving S-S Bond Cleavage of Disulfides and Sulfer. |
| 16. |
Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P-P Bond Cleavage. |
| 17. |
Rhodium-catalyzed phosphorylation reaction of water-soluble disulfides using hypodiphosphoric acid tetraalky esters in water. |
| 18. |
Reversible Formation of Self-assembly Gels Containing Giant Vesicles in Trifluoromethylbenzene Using Oxymethylenehelicene Oligomers with Terminal C16 Alkyl Groups. |
| 19. |
Optically active iodohelicene derivatives exhibit histamine N-methyl transferase inhibitory activity.. |
| 20. |
Acid-catalyzed synthesis of condensed polycyclic diaryl ethers from arenols. |
| 21. |
Rhodium-Catalyzed Synthesis of Organosulfur Compounds using Sulfur. |
| 22. |
Rhodium-catalyzed synthesis of unsymmetric di(heteroaryl) compounds via heteroaryl exchange reactions. |
| 23. |
Mieko Arisawa, Kyosuke Sawahata, Takuya Ichikawa, Masahiko Yamaguchi, Rhodium-Catalyzed Isomerization and Alkyne Exchange Reactions of 1,4-Dithiins via the 1,2-Ethenedithiolato Rhodium Complex, Organometallics, 37, 3174-3180, 2018.09. |
| 24. |
Rhodium-Catalyzed Synthesis of Dialkyl(Heteroaryl)Phosphine Sulfides by Phosphinylation of Heteroaryl Sulfides. |
| 25. |
Saori Tanii, Mieko Arisawa, Takaya Tougo, Masahiko Yamaguchi, Catalytic Method for the Synthesis of C−N-Linked Bi(heteroaryl)s Using Heteroaryl Ethers and N‐Benzoyl Heteroarenes, Organic Letter, 10.1021/acs.orglett.8b00245, 20, 7, 1756-1759, 2018.04. |
| 26. |
Mieko Arisawa, Kyosuke Sawahata, Tomoki Yamada, Debayan Sarkar, Masahiko Yamaguchi, Rhodium-Catalyzed Insertion Reaction of PhP Group of Pentaphenylcyclopentaphosphine with Acyclic and Cyclic Disulfides, Organic Letters, 10.1021/acs.orglett.7b03825, 20, 4, 938-941, 2018.02, Organophosphorus compounds with a phosphorus atom attached to a phenyl group and two organothio/organoseleno groups were synthesized using the rhodium-catalyzed insertion reaction of the PhP group of pentaphenylcyclopentaphosphine (PhP)5 with acyclic disulfides and diselenides. The method was applied to the synthesis of heterocyclic compounds containing the S-P-S group by the reaction of (PhP)5 and cyclic disulfides such as 1,2-dithietes, 1,2-dithiocane, 1,4,5-dithiopane, and 1,2-dithiolanes.. |
| 27. |
Mieko Arisawa, Saori Tanii, Takeru Tazawa, Masahiko Yamaguchi, Synthesis of Unsymmetric HetAr-X-HetAr' Compounds by Rhodium-Catalyzed Heteroaryl Exchange Reactions, Heterocycles, 10.3987/REV-17-869, 94, 12, 2179-2207, 2017.10. |
| 28. |
Saori Tanii, Mieko Arisawa, Takaya Tougo, Kiyofumi Horiuchi, Masahiko Yamaguchi, Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl) Ethers Using Heteroaryl Exchange Reaction, Synlett, 10.1055/s-0036-1588801, 28, 13, 1601-1607, 2017.08. |
| 29. |
Tsukasa Sawato, Atsushi Yagi, Mieko Arisawa, Masahiko Yamaguchi, Chemical braking exhibited by ethynylhelicene (M)-nonamer in solution: Competitive reaction system of self-catalysis to form double-helix and approach towards equilibrium to form random-coil, Tetrahedron, 10.1016/j.tet.2017.03.083, 73, 19, 2801-2805, 2017.05. |
| 30. |
Mieko Arisawa, Takeru Tazawa, Saori Tanii, Kiyofumi Horiuchi, Masahiko Yamaguchi, Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl) Sulfides Using Heteroaryl Ethers and S‐Heteroaryl Thioesters via Heteroarylthio Exchange, The Journal of Organic Chemistry, 10.1021/acs.joc.6b02585, 82, 1, 804-810, 2017.01. |
| 31. |
Masahiko Yamaguchi, Mieko Arisawa, Masanori Shigeno, Nozomi Saito, Equilibrum and Nonequilibrium Chemical Reactions of Helicene Oligomers in the Noncovalent Bond Formation, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 10.1246/bcsj.20160133, 89, 10, 1145-1169, 2016.10, Chemical reactions involving noncovalent bond formation are discussed with regard to the equilibrium and nonequilibrium states: An equilibrium-to-equilibirum chemical reaction involves change of equilibrium states by changing the environment; a nonequilibrium-to-equilibrium reaction involves change of metastable state to equilibrium. Complex nature of the chemical reactions, especially in the latter, is shown in terms of the multiple-path nature in the microscopic molecular structure changes and macroscopic concentration changes. Irreversible and reversible nonequilibrium-to-equilibrium chemical reactions are also compared in terms of the multiple-path. Helicene oligomers, which reversibly form double-helix and random-coil by temperature changes, are discussed with regard to the reversible nonequilibrium-to-equilibrium chemical reaction with self-catalysis, where notable chemical phenomena appear under nonequilibrium conditions.. |
| 32. |
Mieko Arisawa, Tomoki Yamada, Saori Tanii, Yuta Kawada, Hisako Hashimoto, Masahiko Yamaguchi, Rhodium-catalyzed P–P bond exchange reaction of diphosphine disulfides, Chemical Communications, 10.1039/c6cc07302f, 52, 93, 13580-13583, 2016.10. |
| 33. |
Mieko Arisawa, Takuya Ichikawa, Saori Tanii, Masahiko Yamaguchi, Synthesis of Symmetrical and Unsymmetrical 1,4-Dithiins by Rhodium-Catalyzed Sulfur Addition Reaction to Alkynes, Synthesis, 10.1055/s-0035-1561452, 48, 18, 3107-3119, 2016.09. |
| 34. |
Mieko Arisawa, Saori Tanii, Takeru Tazawa, Masahiko Yamaguchi, Rhodium-Catalyzed Transformation of Heteroaryl Aryl Ethers to Heteroaryl Fluorides, 10.1039/c6cc05400e, 52, 76, 11390-11393, 2016.08. |
| 35. |
Mieko Arisawa, Saori Tanii, Tomoki Yamada, Masahiko Yamaguchi, Palladium-catalyzed addition reaction of thioesters to norbornenes, TETRAHEDRON, 10.1016/j.tet.2015.05.042, 71, 37, 6449-6458, 2015.09, A palladium complex derived from Pd-2(dba)(3) and tris(2,4,6-trimethoxyphenyl)phosphine catalyzes the addition reaction of thioesters to norbornenes, giving trans-2-acyl -3-organothionorbornanes. The transadducts are predominantly obtained with the acyl group at the endo-position and the organothio group at the exo-position. Aroyl and heteroaroyl thioesters as well as alkanoyl thioesters were reacted, including S-(4-tolyl) phenylthioglyoxylate and methyl 2-(4-tolylthio)-2-oxo-acetate. (C) 2015 Elsevier Ltd. All rights reserved.. |
| 36. |
Masamichi Miyagawa, Mieko Arisawa, Masahiko Yamaguchi, Equilibrium shift induced by chiral nanoparticle precipitation in rhodium-catalyzed disulfide exchange reaction, TETRAHEDRON, 10.1016/j.tet.2015.05.106, 71, 30, 4920-4926, 2015.07, Chiral silica (P)-nanoparticles grafted with (P)-helicene recognize the molecular structure of a chiral diol disulfide in the presence of monool disulfide and dibutyl disulfide. The (P)-nanoparticles selectively adsorb the diol disulfide, aggregate, and precipitate from solution. Under rhodium-catalyzed equilibrium among three disulfides, the diol disulfide is removed from solution by precipitation, which induces an equilibrium shift in the solution. By conducting the precipitation experiment twice, we obtained the dial disulfide in 37% yield from a statistical 1:2:1 equilibrium mixture of three disulfides. The method is applied to a racemic monool disulfide, and an optically active dial disulfide is obtained via kinetic resolution and equilibrium shift. (C) 2015 Elsevier Ltd. All rights reserved.. |
| 37. |
Mieko Arisawa, Yuri Nihei, Masahiko Yamaguchi, RHODIUM-CATALYZED 2-METHYLTHIOLATION REACTION OF THIAZOLES/OXAZOLES USING 2-(METHYLTHIO)THIAZOLE, HETEROCYCLES, 10.3987/COM-14-S(K)59, 90, 2, 939-949, 2015.01, RhH(PPh3)(4) and 1,3-bis(dicyclohexyl)phosphinopropane (dcypp) catalyze the 2-methylthiolation of oxazoles and thiazoles using 2-(methylthio)thiazole as a thiolating reagent. The methylthio transfer reaction is under equilibrium, and various 2-methylthiolated thiazoles and oxazoles were obtained in moderate to good yields by removing thiazole under refluxing o-dichlorobenzene.. |
| 38. |
Mieko Arisawa, Synthesis of organosulfides using Synthesis of organosulfides using transition-metal-catalyzed substitution reactions: to construct exergonic reactions employing metal inorganic and organic co-substrate/co-product methods, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2014.04.081, 55, 23, 3391-3399, 2014.06, A catalyst changes the course of a reaction without affecting the relative thermodynamic stability of substrates and products, and a catalytic reaction must be exergonic in order to obtain high yields of the product and to attain reasonable reaction rates. In the case that the desired reaction is in equilibrium or is endergonic, devices for making products thermodynamically more stable than substrates are needed. In this review, the transition-metal-catalyzed synthesis of organosulfides using a substitution reaction is summarized, where metal inorganic and organic co-substrate/co-product methods are used in developing exergonic reactions. (C) 2014 Published by Elsevier Ltd.. |
| 39. |
Mieko Arisawa, Takuya Ichikawa, Masahiko Yamaguchi, Synthesis of unsymmetrical polyfluorinated diaryl sulfides by rhodium-catalyzed aryl exchange reaction, Tetrahedron Letters, 10.1016/j.tetlet.2013.06.021, 54, 32, 4327-4329, 2013.08, RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyze the aryl exchange reaction of polyfluorinated diaryl sulfides. By employing these catalysts, unsymmetrical polyfluorinated diaryl sulfides are synthesized by the reaction of symmetrical polyfluorinated diaryl sulfides and substituted pentafluorobenzenes in the presence of triisopropylsilane. © 2013 Elsevier Ltd. All rights reserved.. |
| 40. |
Guangzhe Li, Mieko Arisawa, Masahiko Yamaguchi, Rhodium-catalyzed synthesis and reactions of N-acylphthalimides, Asian Journal of Organic Chemistry, 10.1002/ajoc.201300094, 2, 11, 983-988, 2013.06, A complex of [RhH(PPh3)4] and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyzes the syntheses and reactions of N-acylphthalimides. N-Acylphthalimides were synthesized by the imidation of thioesters or acid fluorides by N-(organothio)phthalimides. CN bond cleavage in N-acylphthalimides was also catalyzed by the same rhodium complex. Thioesters and N-(phosphinoyl)phthalimides were obtained from reactions with phosphinothioates
acid fluorides and N-(tetrafluoroaryl)phthalimides were obtained from reactions with substituted pentafluorobenzenes. © 2013 WILEY-VCH Verlag GmbH &
Co. KGaA, Weinheim.. |
| 41. |
Mieko Arisawa, Guangzhe Li, Masahiko Yamaguchi, Rhodium-catalyzed synthesis of 2,3-diaryl-1,4-diketones via oxidative coupling of benzyl ketones using α-thioketone oxidizing reagent, Tetrahedron Letters, 10.1016/j.tetlet.2012.12.107, 54, 10, 1298-1301, 2013.03, RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyzed the oxidative coupling reaction of aryl benzyl ketones giving 2,3-diaryl-1,4-diketones in high yields. 3,3-Dimethyl-1-methylthio-2-butanone was used as the oxidizing reagent, which was converted to 3,3-dimethyl-2- butanone and dimethyl disulfide. Rhodium enolates were catalytically formed from ketones, which underwent oxidative coupling using an organosulfur reagent. © 2013 Elsevier Ltd. All rights reserved.. |
| 42. |
Mieko Arisawa, Soichiro Nakane, Manabu Kuwajima, Masahiko Yamaguchi, RHODIUM-CATALYZED SYNTHESIS OF BENZOFURANS BY THE REACTION OF KETONES AND O-DIFLUOROBENZENES, HETEROCYCLES, 10.3987/COM-12-S(N)57, 86, 2, 1103-1118, 2012.12, In the presence of catalytic amounts of RhH(PPh3)(4) and 1,2-bis(diphenylphosphino)ethane (dppe), ketones reacted with o-difluorobenzenes giving benzofurans in high yields. The alpha-arylation of ketones and furan cyclization proceeded without using a base. Benzofuran cyclization was applied to substituted pentafluorobenzenes to give 6-substituted-4,5,7-trifluorobenzofuranes.. |
| 43. |
Mieko Arisawa, Takuya Ichikawa, Masahiko Yamaguchi, Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides, ORGANIC LETTERS, 10.1021/ol302497m, 14, 20, 5318-5321, 2012.10, Substituted pentafluorobenzenes react with sulfur to give bis(4-substituted 2,3,5,6-tetrafluorophenyl) sulfides in the presence of RhH(PPh3)(4), 1,2-bis(diphenylphosphino)benzene (dppBz), and tributylsilane. The reaction proceeds efficiently between room temperature and 80 degrees C. A comparative study of the reactivities of an organic trisulfide and a tetrasulfide showed notable substrate specificity. Di-tert-butyl tetrasulfide reacted with reactive aryl monofluorides and substituted pentafluorobenzenes. Di-tert-butyl trisulfide reacted with aryl monofluorides. The reactivity was explained on the basis of the difference in S-S bond energy.. |
| 44. |
Mieko Arisawa, Yuri Nihei, Masahiko Yamaguchi, Rhodium-catalyzed arylthiolation reaction of nitroalkanes, diethyl malonate, and 1,2-diphenylethanone with diaryl disulfides: control of disfavored equilibrium reaction, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2012.07.132, 53, 43, 5729-5732, 2012.10, In the presence of catalytic amounts of RhH(PPh3)(4) and 1,2-bis(diphenylphosphino)ethane (dppe), 1-nitroalkanes reacted with a diaryl disulfide giving 1-arylthio-1-nitroalkanes in air. The equilibrium to form thermodynamically disfavored products was shifted by the rhodium-catalyzed oxidation of thiols to disulfides and water. The thiolation reaction of cyclic nitroalkanes proceeded in high yields provided that suitable diaryl disulfides were employed depending on the substrate: di(p-chlorophenyl) disulfide was used for the thiolation reaction of 1-nitroalkanes, 1-nitrocyclopentane and 1-nitrocycloheptane with acidic alpha-protons (pK(a) 16 and 17); di(p-methoxyphenyl) disulfide for 1-nitrocyclobutane and 1-nitrocyclohexane with less acidic alpha-protons (pK(a) ca. 18). Related reactivities were observed in the thiolation reactions of malonate and 1,2-diphenylethanone. (C) 2012 Elsevier Ltd. All rights reserved.. |
| 45. |
Mieko Arisawa, Manabu Kuwajima, Fumihiko Toriyama, Guangzhe Li, Masahiko Yamaguchi, Rhodium-Catalyzed Acyl-Transfer Reaction between Benzyl Ketones and Thioesters: Synthesis of Unsymmetric Ketones by Ketone CO-C Bond Cleavage and Intermolecular Rearrangement, ORGANIC LETTERS, 10.1021/ol3017148, 14, 14, 3804-3807, 2012.07, In the presence of catalytic amounts of RhH(CO)(PPh3)(3) and 1,2-bis(diphenylphosphino)benzene (dppBz), acyl groups were transferred between benzyl ketones and thioesters/aryl esters. The rhodium complex catalyzed the cleavage of ketone CO-C bonds and intermolecular rearrangement giving unsymmetric ketones. The acyl-transfer reaction also occurred with 1-(p-chloropheny1)-3-(p-cyanophenyl)propane-2-one giving unsymmetric ketones.. |
| 46. |
Mieko Arisawa, Yuri Nihei, Takaaki Suzuki, Masahiko Yamaguchi, Rhodium-Catalyzed Cleavage Reaction of Aryl Methyl Ethers with Thioesters, ORGANIC LETTERS, 10.1021/ol2033724, 14, 3, 855-857, 2012.02, A rhodium complex catalyzed the reaction of aryl methyl ethers and thioesters giving the corresponding aryl esters and methyl sulfides. S-(p-Chlorophenyl) p-(dimethylamino)benzothioate was used for the reaction of methyl aryl ethers with electron-withdrawing groups, and an S-(p-tolyl) derivative was used for those with electron-donating groups. Polymethoxybenzenes were converted to the esters in a regioselective manner.. |
| 47. |
Mieko Arisawa, Yui Igarashi, Haruki Kobayashi, Toru Yamada, Kentaro Bando, Takuya Ichikawa, Masahiko Yamaguchi, Equilibrium shift in the rhodium-catalyzed acyl transfer reactions, TETRAHEDRON, 10.1016/j.tet.2011.07.031, 67, 40, 7846-7859, 2011.10, Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio)pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes. (C) 2011 Published by Elsevier Ltd.. |
| 48. |
Mieko Arisawa, Fumihiko Toriyama, Masahiko Yamaguchi, An Activated Catalyst RhH(PPh3)4-dppe-Me2S2 for α-Methylthiolaton of α-Phenyl Ketones, HETEROATOM CHEMISTRY, 10.1002/hc.20650, 22, 1, 18-23, 2011.09, In the presence of catalytic amounts of RhH(PPh3)(4), 1, 2-bis(diphenylphosphino)ethane (dppe), and dimethyl disulfide, cyclic and acyclic alpha-phenyl ketones reacted with p-cyano-alpha-methylthioacetophenone giving alpha-methylthio-alpha-phenylketones. The activated catalyst containing dimethyl disulfide was effective for the alpha-methylthiolation reaction of these less reactive substrates. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 22:18-23, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20650. |
| 49. |
Hidetsura Cho, Yoshizumi Yasui, Satoshi Kobayashi, Eunsang Kwon, Mieko Arisawa, Masahiko Yamaguchi, SYNTHESIS AND SUBSTITUTION REACTIONS OF 4(6)-CHLORODIHYDROPYRIMIDINES, HETEROCYCLES, 10.3987/COM-11-12244, 83, 8, 1807-1818, 2011.08, Chlorination of the corresponding ketones with phenylphosphonic dichloride (PhPOCl2) provided ethyl 6(4)-chloro-2-methyl-4(6)-phenyl-1,4(6)dihydropyrimidine-5-carboxylate in good yield. The cross-coupling reactions of organoboronic acids or triethylborane with 1-tert-butyl 5-ethyl 4-chloro-2-methyl-6-phenyl-1,6-dihydropyrimidine-1,5-dicarboxylate synthesized by regiospecific alkoxycarbonylation of the chlorinated dihydropyrimidine afforded 1,4(3,4)-dihydropyrimidines having a variety of functional groups at position-6(4) in good to excellent yields.. |
| 50. |
Mieko Arisawa, Takuya Watanabe, Masahiko Yamaguchi, Direct transformation of organosulfur compounds to organophosphorus compounds: rhodium-catalyzed synthesis of 1-alkynylphosphine sulfides and acylphosphine sulfides, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2011.02.112, 52, 18, 2410-2412, 2011.05, A rhodium-catalyzed method for the synthesis of organophosphorus compounds directly from organosulfur compounds was developed. In the presence of RhH(PPh3)(4) and depe, the reaction of 1-alkylthioalkynes with tetraethyldiphosphine disulfide gave 1-alkynylphosphine sulfides. The same complex catalyzed the reaction of thioesters giving acylphosphine sulfides. (C) 2011 Published by Elsevier Ltd.. |
| 51. |
Mieko Arisawa, Fumihiko Toriyama, Masahiko Yamaguchi, Rhodium-catalyzed phenylthiolation reaction of heteroaromatic compounds using alpha-(phenylthio)isobutyrophenone, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2011.02.077, 52, 18, 2344-2347, 2011.05, In the presence of catalytic amounts of RhH(PPh3)(4) and 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-benzothiazoles, 1,3-benzoxazoles, and benzothiophene reacted with alpha-(phenylthio)isobutyrophenone giving 2-phenylthio derivatives. Reactive monocyclic heteroaromatics, 1-methyl-1,2,3,4-tetrazole and 2-cyanothiophene were also converted into the 5-phenylthio derivatives. The use of an appropriate phenylthio transfer reagent is crucial for the efficient catalyzed conversion of heteroaromatic C-H bonds into C-S bonds. (C) 2011 Published by Elsevier Ltd.. |
| 52. |
Mieko Arisawa, Fumihiko Toriyama, Masahiko Yamaguchi, Rhodium-catalyzed α-methylthiolation reaction of unactivated ketones using 1,2-diphenyl-2-methylthio-1-ethanone for the methylthio transfer reagent, TETRAHEDRON, 10.1016/j.tet.2011.01.071, 67, 12, 2305-2312, 2011.03, In the presence of catalytic amounts of RhH(PPh(3))(4), 1,2-bis(diphenylphosphino)ethane (dppe), and dimethyl disulfide, ketones without alpha-activating groups were alpha-methylthiolated with 1,2-diphenyl-2methylthio-1-ethanone giving alpha-methylthio ketones. The reaction of unsymmetrical ketones proceeded at the more substituted carbons. The initial formation of kinetic alpha-methylthiolated products followed by their rearrangement to thermodynamic products was observed in the reaction of alpha-phenyl ketones. Aldehydes, phenylacetate, and phenylacetonitrile were also alpha-methylthiolated under these conditions. (C) 2011 Published by Elsevier Ltd.. |
| 53. |
Mieko Arisawa, Yui Igarashi, Yoko Tagami, Masahiko Yamaguchi, Chizuko Kabuto, Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2010.12.065, 52, 8, 920-922, 2011.02, A rhodium complex derived from RhH(PPh(3))(4) and Me(2)PhP catalyzed the carbothiolation reaction of 1-alkylthio-1-alkynes and 1,4-diaryl-1,3-butadiynes giving (Z)-4-alkylthio-4-aryl-3-arylethynyl-3-buten-1-ynes. Terminal alkynes such as 1-decyne and (t-butylthio)acetylene underwent the carbothiolation reaction using a RhH(PPh(3))(4)-dppb catalyst. The reactions proceeded via cis-addition with C-C bond formation at the less hindered acetylene carbon. (C) 2011 Published by Elsevier Ltd.. |
| 54. |
Mieko Arisawa, Toru Yamada, Masahiko Yamaguchi, Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2010.09.009, 51, 47, 6090-6092, 2010.11, A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh3)(4)-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6-tetrafluorobenzenes. (C) 2010 Published by Elsevier Ltd.. |
| 55. |
Arisawa M, Toriyama F, Yamaguchi M, Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides., Chemical and pharmaceutical bulletin, 10.1248/cpb.58.1349, 58, 10, 1349-1352, 2010.10. |
| 56. |
Mieko Arisawa, Masahiko Yamaguchi, Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2010.07.040, 51, 37, 4840-4842, 2010.09, Transition metal complexes catalyzed the dialkylphosphinothioation reaction of alcohols and phenols with tetraalkyldiphosphine disulfides in high yields. Phenols were reacted in the presence of RhH(PPh(3))(4) and 1,2-bis(dimethylphosphino)ethane under THF reflux, and alcohols with Pd(OAc)(2) and 1,2-bis(diphenylphosphino)benzene under chlorobenzene reflux. Primary alcohols reacted faster than secondary alcohols under these conditions, and protected tyrosine and serine were phosphinothioated with minimal racemization. Tetraphenyldiphosphine dioxide also underwent the P-O bond formation reaction. (C) 2010 Published by Elsevier Ltd.. |
| 57. |
Mieko Arisawa, Toru Yamada, Masahiko Yamaguchi, Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2010.07.038, 51, 38, 4957-4958, 2010.09, A rhodium complex catalyzed the reaction of acid fluorides and tetraethyldiphosphine disulfide giving acylphosphine sulfides. Aromatic acid fluorides with electron donating p-groups reacted smoothly giving the products in high yields. Aliphatic acid fluorides with secondary and tertiary a-carbons were also converted to alkanoylphosphine sulfides, whereas the reaction of a substrate with an a-methylene carbon was accompanied by enol ester formation. (C) 2010 Published by Elsevier Ltd.. |
| 58. |
Mieko Arisawa, Manabu Kuwajima, Masahiko Yamaguchi, Synthesis of o-(diphenylphosphinoyloxy)anilines by the rhodium-catalyzed reaction of nitroarenes and diphenylphosphine oxide, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2010.04.029, 51, 23, 3116-3118, 2010.06, A rhodium complex Rh(2)(OAc)(4) catalyzed the reaction of nitrobenzenes and diphenylphosphine oxide HP(=O)Ph(2) giving o-(diphenylphosphinoyloxy)anilines predominantly, which were accompanied by small amounts of the p-isomers. Nitorobenzenes possessing a bulky o-substituent, particularly o-(t-butyl)nitrobenzenes, underwent the reaction in high yields. The reaction is considered to involve the reductive formation of O-phosphinoyl-N-arylhydroxyamines from nitrobenzenes, and o-phosphinoyloxylation by the rearrangement. (C) 2010 Elsevier Ltd. All rights reserved.. |
| 59. |
Mieko Arisawa, Manabu Kuwajima, Atsushi Suwa, Masahiko Yamaguchi, RhCl3-CATALYZED DISULFIDE EXCHANGE REACTION OF INSULIN AND DITHIODIGLYCOLIC ACID, HETEROCYCLES, 10.3987/COM-09-S(S)110, 80, 2, 1239-1248, 2010.03, RhCl3 catalyzed the alkylthio exchange reaction of insulin and dithiodiglycolic acid in water under homogeneous conditions. Insulin was rapidly consumed, and mono- and bis-exchanged insulin were formed along with the disulfide exchanged A and B chain. The disulfide bond at the A7/B7 was initially exchanged, which was followed by the A6/A11 and A20/B19 disulfides.. |
| 60. |
Mieko Arisawa, Masahiko Yamaguchi, Rhodium-catalyzed addition reaction of diphosphine disulfide to aldehydes and ketones, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2009.03.135, 50, 26, 3639-3640, 2009.07, In the presence of RhH(PPh(3))(4) and 1,2-bis(diphenylphosplino)ethane, tetramethyldiphosphine disulfide and aldehydes were added producing [1-(dimethylthiophosphosphinoyloxy)alkyl]dimethylphosphine sulfides in high yields. Acetophenones with electron-withdrawing P-groups also yielded 1,2-adducts. (C) 2009 published by Elsevier Ltd.. |
| 61. |
Mieko Arisawa, Katsunori Suwa, Tomofumi.Ishikawa, Masahiko Yamaguchi, Rhodium-Catalyzed Methylthio Transfer Reaction between Ketone α-Positions: Reversible Single-Bond Metathesis of C-S and C-H Bonds, 10.1021/ol802619e, 11, 3, 625-627, 2009.02. |
| 62. |
Mieko Arisawa, Masahiko Yamaguchi, Rhodium-catalyzed thiophosphinoylation reaction of 1,2-dienes with diphosphine disulfides, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2008.10.075, 50, 1, 45-47, 2009.01, In the presence of RhH(PPh(3))(4), the reaction of 1,2-alkadienes, tetramethyldiphosphine disulfide, and camphorsulfonic acid gave (E)-2-dimethylthiophosphinoyl-2-alkenes. The reaction involved the P-P cleavage and the transfer of the thiophosphinoyl group to 1,2-alkadienes with concomitant formation of thiophosphinic anhydride. (C) 2008 Elsevier Ltd. All rights reserved.. |
| 63. |
Mieko Arisawa, Takaaki Suzuki, Tomofumi Ishikawa, Masahiko Yamaguchi, Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides: p-orientation in the polyarylthiolation of polyfluorobenzenes, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 10.1021/ja8049996, 130, 37, 12214-12215, 2008.09, In the presence of a catalytic amount of RhH(PPh(3))(4) and 1,2-bis (diphenylphosphino)benzene, an aromatic fluoride, an organic disulfide (0.5 equiv), and triphenylphosphine (0.5 equiv) reacted in refluxing chlorobenzene to give an aryl sulfide in high yield. Since triphenylphosphine trapped fluoride atoms forming phosphine difluoride, both organothio groups of the disulfide reacted effectively, and the fluoride substituent reacted more readily than the chloride and bromide. The reaction of hexafluorobenzene and a diaryl disulfide gave 1,4-diarylthio-2,3,5,6-tetrafluorobenzene, 1,2,4,5-tetraarylthio-3,6-difluorobenzene, and hexaarylthiobenzene in a stepwise manner; pentafluorobenzene gave 1-arthio-2,3,5,6-tetrafluorobenzene; 1,2,3,4-tetrafluorobenzene gave 1,2-diarylthio-3,6-difluorobenzene; and 1,2,4,5-tetrafluorobenzene gave 1,4-diarylthio-2-5-difluorobenzene. The polyarylthiolation reaction of polyfluorobenzenes exhibited a strong tendency to form 1,4-difiuorobenzenes.. |
| 64. |
Mieko Arisawa, Masahiko Yamaguchi, Transition-metal-catalyzed synthesis of organosulfur compounds, PURE AND APPLIED CHEMISTRY, 10.1351/pac200880050993, 80, 5, 993-1003, 2008.05, Rhodium complexes are efficient catalysts for the synthesis of organosulfur compounds. They catalyze the addition reaction of organosulfur groups to unsaturated compounds, the substitution of C-H with organosulfur groups, and single-bond metathesis reactions. They cleave S-S bonds and transfer the organosulfur groups to various organic and inorganic molecules, including alkynes, allenes, disulfides, sulfur, isonitriles, imines, diphosphines, thiophosphinites, hydrogen, 1-alkylthio-1-alkynes, thioesters, and allyl sulfides.. |
| 65. |
Mieko Arisawa, Tomohiro Kubota, Masahiko Yamaguchi, Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2008.01.109, 49, 12, 1975-1978, 2008.03, The Wilkinson complex RhCl(PPh(3))(3) catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh(3))(3) (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide. (c) 2008 Elsevier Ltd. All rights reserved.. |
| 66. |
Mieko Arisawa, Yoko Tagami, Masahiko Yamaguchi, Two types of rhodium-catalyzed CS/CS metathesis reactions: formation of CS/CS bonds and CC/SS bonds, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2008.01.040, 49, 10, 1593-1597, 2008.03, A rhodium complex catalyzes two types of single bond metathesis reactions of two CS bonds depending on the added ligand: CS/CS to CS/CS metathesis and CS/CS to CC/SS metathesis. In the presence of a catalytic amount of RhH(PPh(3))(4) and 1,1 '-bis(diphenylphosphino)ferrocene (dppf), two 1-alkylthioalkynes exchange alkylthio groups to give equilibrium mixtures of four 1-alkylthioalkynes. When tris(p-methoxyphenyl)phosphine or diphenylmethylphosphine is used, 1,3-butadiynes are obtained. (c) 2008 Elsevier Ltd. All rights reserved.. |
| 67. |
Transition-Metal-Catalyzed Synthesis of Organophosphorous and Organosulfur Compounds. |
| 68. |
Mieko Arisawa, Masato Onoda, Chieko Hori, Masahiko Yamaguchi, Rhodium-catalyzed synthesis of 1-alkynylphosphine oxides from 1-alkynes and tetraphenylbiphosphine, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2006.04.158, 47, 29, 5211-5213, 2006.07, A rhodium complex RhH(PPh3)(4) catalyzes the C-P bond forming reaction of 1-alkynes and tetrapbenylbiphosphine in the presence of 2,4-dimethylnitro benzene giving 1-alkynylphosphines and its oxides. (c) 2006 Elsevier Ltd. All rights reserved.. |
| 69. |
M Arisawa, A Suwa, M Yamaguchi, RhCl3-catalyzed disulfide exchange reaction using water solvent in homogeneous and heterogeneous systems, JOURNAL OF ORGANOMETALLIC CHEMISTRY, 10.1016/j.jorganchem.2005.11.049, 71, 1159-1168, 2006.03, RhCl3 catalyzed the alkylthio exchange reaction of hydrophilic disulfides in water under homogeneous conditions, and equilibrium was attained in several hours. The reaction was applied to the exchange Of unprotected glutathione disulfide. The reaction of dimethyl disulfide and hydrophilic distilfides under heterogeneous conditions also proceeded effectively. The mechanism turned out to be dependent on the water solubility of the substrates: The reaction of bis(3-hydroxypropyl) disulfide took place in the dimethyl disulfide phase, whereas the reaction of bis(6-aminohexyl) disulfide dihydrochloride proceeded in the water phase. (c) 2005 Elsevier B.V. All rights reserved.. |
| 70. |
M Arisawa, M Yamaguchi, Palladium-catalyzed synthesis of 1-alkylphosphonium salts from 1-alkenes, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 10.1021/ja055775s, 128, 1, 50-51, 2006.01. |
| 71. |
M Arisawa, K Fujimoto, S Morinaka, M Yamaguchi, Equilibrating C-S bond formation by C-H and S-S bond metathesis. Rhodium-catalyzed alkylthiolation reaction of 1-alkynes with disulfides, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 10.1021/ja0527121, 127, 35, 12226-12227, 2005.09. |
| 72. |
M Arisawa, C Sugata, M Yamaguchi, Oxidation/reduction interconversion of thiols and disulfides using hydrogen and oxygen catalyzed by a rhodium complex, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2005.06.169, 46, 36, 6097-6099, 2005.09, RhH(PPh3)(4) catalyzes reduction of disulfides to thiols by hydrogen and RhH(PPh3)(4)/1,4-bis(diphenylphosphino)butane (dppb) catalyzes oxidation of thiols to disulfides by oxygen. (c) 2005 Elsevier Ltd. All rights reserved.. |
| 73. |
M Arisawa, T Ono, M Yamaguchi, Rhodium-catalyzed thiophosphinylation and phosphinylation reactions of disulfides and diselenides, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2005.06.109, 46, 34, 5669-5671, 2005.08, Alkyl and aryl dithiophosphinates were synthesized by the reaction of disulfides with biphosphine disulfides in the presence of RhH(PPh3)(4) and 1,2-diphenylphosphinoethane (dppe). The catalyst also promoted synthesis of thiophosphinates and selenothiophosphinates from disulfides and diselenides. (c) 2005 Elsevier Ltd. All rights reserved.. |
| 74. |
M Arisawa, K Tanaka, M Yamaguchi, Rhodium-catalyzed sulfur atom exchange reaction between organic polysulfides and sulfur, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2005.05.024, 46, 28, 4797-4800, 2005.07, RhH(PPh3)(4) and cis-1,2-bis(diphenylphosphino)ethylene (dppv) catalyze the exchange of sulfur atoms between sulfur and organic polysulfides. The exchange of dialkyl trisuffides with sulfur proceeds at a high efficiency within 5 min at room temperature yielding a mixture of organic polysulfides. (c) 2005 Elsevier Ltd. All rights reserved.. |
| 75. |
M Arisawa, M Ashikawa, A Suwa, M Yamaguchi, Rhodium-catalyzed synthesis of isothiocyanate from isonitrile and sulfur, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2005.01.069, 46, 10, 1727-1729, 2005.03, Rhodium complexes RhH(PPh3)(4) and Rh(acac)(CH2=CH2)(2) catalyze sulfuration of isonitrile with sulfur giving isothiocyanates in high yields. The metal-catalyzed reaction is rapid in refluxing acetone, and completes within 3 h in most cases. The reaction exhibits induction period, which disappeared by preheating sulfur in refluxing acetone for 1.5 h. Use of several organic polysulfides in this transformation was examined in order to compare the reactivity. (C) 2005 Elsevier Ltd. All rights reserved.. |
| 76. |
R Amemiya, A Fujii, M Arisawa, M Yamaguchi, GaCl3-catalyzed alpha-ethynylation reaction of silyl enol ethers, JOURNAL OF ORGANOMETALLIC CHEMISTRY, 10.1016/S0022-328X(03)00456-X, 686, 1-2, 94-100, 2003.11, GaCl3 catalyzes alpha-ethynylation reaction of silyl enol ethers with triethylsilylated chloroethyne at 130 degreesC. (C) 2003 Elsevier B.V. All rights reserved.. |
| 77. |
M Arisawa, Y Kozuki, M Yamaguchi, Rhodium-catalyzed regio- and stereoselective 1-seleno-2-thiolation of 1-alkynes, JOURNAL OF ORGANIC CHEMISTRY, 10.1021/jo034990t, 68, 23, 8964-8967, 2003.11, Rhodium complex RhH(PPh3)(4) and 1,1'-bis(diphenylphosphino)ferrocene catalyze the regio- and stereoselective additions of diaryl disulfides and diaryl diselenides to 1-alkynes giving (Z)-1-arylseleno-2-arylthio-1-alkenes. The catalyst promotes the addition reaction of dibutyl disulfide and dibutyl diselenide to 1-octyne with a similar selectivity giving (Z)-1-butylseleno-2-butylthio-1-octene but with a lower catalytic activity. The same product is obtained with a higher yield, when excess dibutyl disulfide is used against dibutyl diselenide in the presence of RhH(PPh3)(4) and 1,4-diphenylphosphinobutane.. |
| 78. |
M Arisawa, M Yamaguchi, Rhodium-catalyzed disulfide exchange reaction, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 10.1021/ja035221u, 125, 22, 6624-6625, 2003.06. |
| 79. |
M Arisawa, A Suwa, K Fujimoto, M Yamaguchi, Transition metal-catalyzed synthesis of (E)-2-(Alkylthio)alka-1,3-dienes from allenes and dialkyl disulfides with concomitant hydride transfer, ADVANCED SYNTHESIS & CATALYSIS, 10.1002/adsc.200303010, 345, 5, 560-563, 2003.05, Reaction of dialkyl disulfides or diselenides with allenes is catalyzed by a rhodium-phosphine complex and trifluoromethanesulfonic acid giving (E)-2-alkylthio(seleno)-1,3-dienes and (E)-2-alkylthio(seleno)-2-alkenes. Unlike the reaction of alkynes, the reaction of allene is accompanied by hydride transfer.. |
| 80. |
R Amemiya, A Fujii, M Arisawa, M Yamaguchi, Sequential carbometalation/elimination reaction takes place between gallium enolate and chloroethyne, CHEMISTRY LETTERS, 10.1246/cl.2003.298, 32, 3, 298-299, 2003.03, In the presence of GaCl3, silyl enol ethers are sequentially ethynylated at the a-carbon atom with chlorotrimethylsilyl-ethyne giving (alpha-enynylated, (alpha-endiynylated and alpha-entriynylated ketones.. |
| 81. |
K Kobayashi, M Arisawa, M Yamaguchi, GaCl3-catalyzed ortho-ethynylation of phenols, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 10.1021/ja026108r, 124, 29, 8528-8529, 2002.07. |
| 82. |
M Arisawa, R Amemiya, M Yamaguchi, One-step ethynylation of silyl enol ether with chlorosilylethyne, ORGANIC LETTERS, 10.1021/ol026050l, 4, 13, 2209-2211, 2002.06, In the presence of GaCl3, silyl enol ethers are ethynylated at the alpha-carbon atom with chlorotrimethylsilylethyne. This reaction can provide alpha-ethynylated aryl ketones possessing acidic alpha-protons without isomerization to conjugated allenyl ketones.. |
| 83. |
M Arisawa, R Momozuka, M Yamaguchi, Rhodium catalyzed anti-Markovnikov addition of triphenylphosphine to 1,3-dienes - A novel method to separate pure (Z)-1,3-alkadienes from isomeric mixtures, CHEMISTRY LETTERS, 10.1246/cl.2002.272, 31, 272-273, 2002.03, Rhodium-catalyzed addition of triphenylphosphine and trifluoromethanesulfonic acid to (E)-1,3-dienes gives (E)-3alkenylphosphonium salts in the anti-Markovnikov mode. The addition reactions to (E)-1,3-dienes proceed more rapidly than those to (Z)-1,3-dienes, which can be utilized to separate pure (Z)1,3-dienes from isomeric mixtures.. |
| 84. |
M Arisawa, C Miyagawa, M Yamaguchi, Equatorial preference in the GaCl3-promoted ethenylation of cyclic ketones, SYNTHESIS-STUTTGART, 10.1055/s-2002-19298, 1, 138-145, 2002.01, Silyl enol ethers derived from substituted cyclohexanones are ethenylated with trimethylsilylethyne in the presence of GaCl3. Carbon-carbon bond formation was completed in less than 5 min at room temperature and protodegallation of the organogallium intermediate formed with 6 M sulfuric acid gave beta-enones. The reactions exhibit a bias for the equatorial C-C bond formation, which contrasts the axial stereochemistry of enolate alkylation. The origin of this stereoselectivity is discussed.. |
| 85. |
M Arisawa, C Miyagawa, S Yoshimura, Y Kido, M Yamaguchi, GaCl3-promoted ethenylation of thioester silyl enolate and dienolate with silylethyne, CHEMISTRY LETTERS, 10.1246/cl.2001.1080, 11, 1080-1081, 2001.11, In the presence of GaCl3, silyl enol ethers derived from either S-alkyl or S-aryl thioesters are ethenylated at the alpha -carbon atom with trimethylsilylethyne in high yields. The reactions of dienolates give alpha,alpha -diethenyl thioesters.. |
| 86. |
M Arisawa, M Yamaguchi, Addition reaction of dialkyl disulfides to terminal alkynes catalyzed by a rhodium complex and trifluoromethanesulfonic acid, ORGANIC LETTERS, 10.1021/ol015521l, 3, 5, 763-764, 2001.03, [GRAPHICS]
Addition of dialkyl disulfides to terminal alkynes is catalyzed by a rhodium-phosphine complex and trifluoromethanesulfonic acid giving (Z)-bis(alkylthio)olefins stereoselectively.. |
| 87. |
M Arisawa, K Akamatsu, M Yamaguchi, GaCl3-promoted ethenylation of silylated β-dicarbonyl compound with silylethyne. Synthesis of ethenylmalonate, ORGANIC LETTERS, 10.1021/ol015583b, 3, 5, 789-790, 2001.03, [GRAPHICS]
In the presence of GaCl3, silyl enol ethers derived from alpha -substituted beta -ketoesters or malonates are ethenylated at the alpha -carbon atom with trimethylsilylethyne in high yields. Ethenylmalonates can also be synthesized by this method.. |
| 88. |
M Arisawa, M Yamaguchi, Rhodium-catalyzed Beckmann rearrangement, ORGANIC LETTERS, 10.1021/ol006951z, 3, 2, 311-312, 2001.01, [GRAPHICS]
Beckmann rearrangement of oxime is catalyzed by [RhCl(cod)](2), trifluoromethanesulfonic acid, and tris(p-tolyl)phosphine in refluxing dichloroethane, giving the corresponding amide in good yield. Product/acid ratios of 10:20 can be attained in the reaction of benzophenone oximes.. |
| 89. |
M Arisawa, M Yamaguchi, Stereoselective synthesis of (E)- and (Z)-allylphosphonium salts by palladium-catalyzed addition of phosphine to allene, ADVANCED SYNTHESIS & CATALYSIS, 343, 1, 27-28, 2001.01. |
| 90. |
GaCl3-promoted addition reactions of carbon nucleophiles to alkyne. |
| 91. |
M Arisawa, M Yamaguchi, Metal-catalyzed addition of phosphine and methanesulfonic acid to alkyne, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 122, 10, 2387-2388, 2000.03. |
| 92. |
K Kobayashi, M Arisawa, M Yamaguchi, β-Silylethenylation of phenol with silylethyne using gallium trichloride, INORGANICA CHIMICA ACTA, 296, 1, 67-71, 1999.12, Treatment of lithium phenoxide with silylethyne in the presence of GaCl3 gives o-(beta-silylethenyl)phenol in a high yield. The reaction involves carbogallation of phenoxygallium with silylethyne. The reaction of 2,6-disubstituted phenol with one of the substituents being t-butyl group gives ipso-substitution product. Organometallic compounds of gallium and tin, elements which sit diagonally in the periodic table, behave similarly in the carbometallation reaction. (C) 1999 Elsevier Science S.A. All rights reserved.. |
| 93. |
M Yamaguchi, T Tsukagoshi, M Arisawa, Ethenylation of silyl enol ether with silylethyne, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 121, 16, 4074-4075, 1999.04. |
| 94. |
Novel Aromatic Vinylation Reactions. |
| 95. |
M Yamaguchi, K Kobayashi, M Arisawa, Synthesis of β,β-bis(trimethylstannyl)styrenes by organometal trapping of intermediates in the aromatic vinylation reactions, 12, 1317-1318, 1998.12. |
| 96. |
M Arisawa, T Sugihara, M Yamaguchi, Synthesis of cross-conjugated trienes by dimerization of allenes with palladium-phenol catalyst, CHEMICAL COMMUNICATIONS, 23, 2615-2616, 1998.12, Cross-conjugated trienes were synthesized by dimerization of monosubstituted allenes in the presence of a catalyst system consisted of Pd-2(dba)(3), p-nitrophenol, and P(p-Tol)(3).. |
| 97. |
M Yamaguchi, M Arisawa, K Omata, K Kabuto, M Hirama, T Uchimaru, Ortho-vinylation reaction of phenols with ethyne, JOURNAL OF ORGANIC CHEMISTRY, 10.1021/jo980785f, 63, 21, 7298-7305, 1998.10, Phenols were vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N reagent. The reaction was applicable to phenols possessing either electron-donating or electron-withdrawing groups. 2,6-Divinylphenols were synthesized under modified conditions. A reaction mechanism involving carbostannylation of alkynyltin and phenoxytin was discussed.. |
| 98. |
M Yamaguchi, M Arisawa, M Hirama, ortho-vinylation reaction of anilines, CHEMICAL COMMUNICATIONS, 13, 1399-1400, 1998.07, N-Alkylanilines and anilines are vinylated at the ortho-position with ethyne in the presence of SnCl4-Bu3N.. |
| 99. |
2,6-Divinylation of Phenols with Ethyne. |
