Kyushu University Academic Staff Educational and Research Activities Database
List of Presentations
Ryoichi Kuwano Last modified date:2018.06.21

Professor / Interdisciplinary Chemistry / Department of Chemistry / Faculty of Sciences


Presentations
1. Hydrogenation of Heterocyclic and Carbocyclic Arenes with Asymmetric Catalysis.
2. Ruthenium-Catalyzed Chemo- and Enantioselective Hydrogenation of Isoquinoline Carbocycles.
3. Enantioselective Hydrogenation of Quinolines and Isoquinoline Carbocycles.
4. Palladium-Catalyzed Decarboxylative Coupling of Benzyl Fluorobenzoates.
5. Enantioselective Hydrogenation of Nitrogen-Containing Heteroarenes.
6. Asymmetric Hydrogenation of Heteroarenes.
7. Chemo- and Enantioselective Hydrogenation of Azaindoles.
8. Catalytic Reactions involved with Benzylic C–O Bond Activation by Palladium Complex.
9. Asymmetric Hydrogenation of Aromatic Compound .
10. Ryoichi Kuwano, Enantioselective Hydrogenation of Heterocyclic Arenes, INTERNATIONAL SYMPOSIUM ON PURE & APPLIED CHEMISTRY (ISPAC) 2016, 2016.08, Asymmetric hydrogenation of heteroarenes will offer an attractive access to chiral 5- or 6-membered heterocycles, which are often seen in various useful biologically active compounds. However, the aromaticity of the substrate might have hampered the development of the asymmetric reaction. In this presentation, I will present our recent work on the catalytic asymmetric hydrogenation of heteroarenes, isoxazolium salts and azaindoles. The hydrogenation products, isoxazolines and azaindolines, were successfully obtained in high enantioselectivities..
11. Ryoichi Kuwano, Enantioselective Hydrogenation of Heteroarenes and Arenes, 5th UK-Japanese Symposium on Asymmetric Catalysis, 2016.03, Enantioselective hydrogenation of (hetero)arenes will offer a powerful tool for organic synthesis, because the asymmetric reaction provides various optically active heterocycles. Nowadays, asymmetric catalysis allows various heteroarenes to be transformed into the corresponding chiral heterocycles with high enantiomeric excesses, but many heteroaromatic substrates still remain unexplored in asymmetric hydrogenation. Furthermore, only a few successes have been reported on the asymmetric hydrogenation of carbocyclic arenes.

We have developed the catalytic asymmetric hydrogenations of various heteroarenes by using a trans-chelating chiral bisphosphine, PhTRAP. Recently, we found that the PhTRAP–ruthenium complex catalyzed the hydrogenation of some benzo-fused carbocyclic arenes. The hydrogenations of naphthalenes and quinolines produced chiral tetralins and 5,6,7,8-tetrahydroquinolines with high enantiomeric excesses through the chiral ruthenium catalyst. Concurrently, we have realized the highly enantioselective hydrogenation of pyrimidines with a chiral iridium catalyst. I will disclose our recent studies of this issue in this presentation..
12. Ryoichi Kuwano, Catalytic asymmetric hydrogenation of carbocyclic arenes, The 2015 International Chemical Congress of Pacific Basin Societies (Pacifichem 2015), 2015.12, Stereoselective hydrogenation of arenes,including heteroarenes, will offer an attractive access to chiral 5- or 6-membered cyclic skeletons. Nowadays, various heteroarenes are reduced into chiral fully or partly saturated heterocycles with high enantiomeric excesses by using asymmetric catalysis. Meanwhile, the catalytic asymmetric hydrogenation of carbocyclic arenes has been unexplored as compared to that of heteroarenes. In this presentation, we will reports the catalytic asymmetric hydrogenation of naphthalenes and quinoline carbocycles. In these asymmetric hydrogenations, high enantioselectivities were accomplished by using the ruthenium complex, which contains trans-chelating chiral bisphosphine, PhTRAP (1).

A solution of naphthalene-2,6-dicarboxylate 2 was exposed to pressurized hydrogen gas in the presence of {RuCl(p-cymene)[(S,S)-(R,R)-1]}Cl (3) and DBU. The reaction mixture afforded chiral tetralin 4 with 86% ee (eq. 1). The chiral ruthenium complex 3 converted 2,6- or 2,7-dialkoxynaphthalene 5 to the corresponding hydrogenation product 6 with up to 92% ee (eq. 2).

To our surprise, PhTRAP–ruthenium catalyst selectively transforms quinolines into 5,6,7,8-tetrahydroquinolines, while 1,2,3,4-tetrahydroquinolines are commonly obtained from the hydrogenation of quinolines. Furthermore, the chiral ruthenium catalyst allows the reaction of 8-methoxyquinoline 7 to produce 5,6,7,8-tetrahydroquinoline 8 with 83% ee. .
13. Ryoichi Kuwano, Ryuhei Ikeda, Yusuke Makida, Enantioselective Hydrogenation of Carbocyclic Arenes, 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC 13), 2015.11, Asymmetric hydrogenation of carbocyclic arenes is a formidable subject in organic chemistry, although asymmetric catalysis nowadays allows hydrogenations of various heteroarenes to proceed with high enantioselectivities. In this presentation, we will disclose our recent research on catalytic asymmetric hydrogenation of carbocyclic arenes.

A solution of naphthalene-2,6-dicarboxylate was exposed to pressurized hydrogen gas in the presence of {RuCl(p-cymene)[(S,S)-(R,R)-PhTRAP]}Cl (1) and DBU. The reaction mixture afforded chiral tetralin with 86% ee. The chiral ruthenium complex 1 converted 2,6- or 2,7-dialkoxynaphthalene to the corresponding hydrogenation product with up to 92% ee (eq. 1).

To our surprise, PhTRAP–ruthenium catalyst selectively transforms quinolines into 5,6,7,8-tetrahydroquinolines, while 1,2,3,4-tetrahydroquinolines are commonly obtained from the hydrogenation of quinolines. Furthermore, the chiral ruthenium catalyst allows the reaction of 8-methoxyquinoline to produce 5,6,7,8-tetrahydroquinoline with 83% ee (eq. 2)..
14. Ryoichi Kuwano, Catalytic Asymmetric Hydrogenation of Arenes and Heteroarenes, 18th Malaysian International Chemical Congress, 2014.11.
15. Ryoichi Kuwano, Yushu Jin, Sadakazu Komiya, Masakazu Ohtsubo, Satoshi Ueno, Kentaro Ishizuka, Catalytic Cyclizations through Benzylic C–O Bond Cleavage with Palladium Catalysis, XXVI International Conference on Organometallic Chemistry, 2014.07.
16. Ryoichi Kuwano, Ryuhei Ikeda, Yuta Hashiguchi, Kentaro Ishizuka, Catalytic Asymmetric Hydrogenation of Heteroarenes and Arenes, 20th International Conference on Phosphorus Chemistry, 2014.06.
17. 金 玉樹, 石塚 賢太郎, 桑野 良一, An Improvement of Palladium Catalyst for the [4+2] Cycloaddition of o-(Silylmethyl)- benzyl Carbonate with Alkenes, 日本化学会第94春季年会, 2014.03.
18. Ryoichi Kuwano, Catalytic Asymmetric Hydrogenation of Heteroarenes and Arenes, International Symposium on Catalysis & Fine Chemicals 2013, 2013.12.
19. Ryoichi Kuwano, Ryuhei Ikeda, Catalytic Asymmetric Hydrogenation of Naphthalenes and Quinolines, 20th EuCheMS Conference on Organometallic Chemistry, 2013.07.
20. 桑野 良一, Nao Kameyama, Ryuhei Ikeda, Kazuki Hirasada, Manabu Kashiwabara, Catalytic Asymmetric Hydrogenation of Heteroarenes and Arenes with Chiral Ruthenium Complex, Cambodian Malaysian Chemical Conference (CMCC) 2012, 2012.10.
21. Ruthenium-Catalytic Asymmetric Hydrogenation of Benzisoxazoles.
22. One-Pot Synthesis of Substituted Pyridines by Nickel-Catalyzed Carbon–Carbon Bond Formation of Saturated Ketones at the β-Position with Enamines.
23. Palladium-Catalyzed Intramolecular Mizoroki–Heck Reaction of Benzylic Esters.
24. Carbon‒Nitrogen Bond Formation at the δ-Position through a Sequential Palladium-Catalyzed Dehydrogenation of Butyl Ketones.
25. Synthesis of .beta.-Enaminonitrile via Palladium-Catalyzed Dehydrogenation of Saturated Nitriles.
26. Carbon-Nitrogen Bond Formation at the .delta.-Position through Palladium-Catalyzed Dehydrogenation of .beta.,.gamma.-Unsaturated Carbonyl Compounds.
27. Ruthenium-Catalyzed Asymmetric Hydrogenation of Oxazoles.
28. Palladium-Catalyzed Benzylic Substitution of Benzylic Carbonates with Phosphorus Compounds.
29. Palladium-Catalyzed [3+2] Cycloaddition of m-(Silylmethyl)benzylic Carbonates with Electron-Deficient Alkenes.
30. Palladium-catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzylic Esters with Double Bonds: an Equivalent of Diels–Alder Reaction of o-Xylylenes.
31. Rhodium-Catalyzed Carbon–Carbon Bond Forming Reactions of Arylboronic Acids with Alkenyl Acetates.
32. Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Esters with Ketones.
33. Transformation of Benzyl Benzoates into Diarylmethanes through Palladium-Catalyzed Decarboxylation.
34. Palladium-Catalyzed Oxidative Functionalization at the beta-Position of Alkyl Ketones.
35. Rhodium-Catalyzed cine-Selective Cross-Coupling of Alkenyl Acetates with Organoboron Compounds.
36. Palladium-Catalyzed Intramolecular Aromatic Nucleophilic Substitution of Benzyl Esters.
37. Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Esters with Imines.
38. Nickel-Catalyzed Intramolecular Oxidative Amination of Ketones.
39. gamma-Amination of Alcohols: Nickel-Catalyzed Oxidative Amination of alpha-Substituted Propanols.
40. Nickel-Catalyzed Oxidative Amination of Ethyl Ketones at the beta-Position.
41. Highly Active Palladium Catalyst for the Cross-Coupling of Benzylic Carbonates with Arylboronic Acids.
42. Rhodium-Catalyzed Cross-Coupling of Vinyl acetates with Arylboron Compounds.
43. Catalytic Asymmetric Hydrogenation of Imidazoles.
44. Catalytic Asymmetric Hydrogenation of 2,4-Disubstituted Pyrroles.
45. Catalytic Asymmetric Hydrogenation of Aromatic Compounds.
46. Ruthenium-Catalyzed Asymmetric Hydrogenation of Quinolines, Which were Reduced on the Benzene Ring..
47. Ruthenium-Catalyzed Asymmetric Hydrogenation of Naphthalenes.
48. Nickel-Catalyzed Oxidative Amination of Carbonyl Compounds Involved with the beta-Carbon-Nitrogen Formation.
49. Nickel-Catalyzed Dimerization and Oxidative Amination of Carbonyl Compounds at the beta-Position.
50. Palladium-catalyzed Cross-coupling of Benzylic Carbonates with Organometallic Compounds.
51. Transformations of ubiquitous functional group, carboxylate.
52. Advanced Molecular Transformations of Benzylic Esters.
53. Palladium-Catalyzed Decarboxylative Etherification of Aryl Benzyl Carbonates
Hiroki Kusano, Ryoichi Kuwano
88th Annual Meeting of the Chemical Society of Japan.
54. Palladium-Catalyzed Decarboxylative Benzylation of β-Keto Esters
Kenta Ushijima, Ryoichi Kuwano
88th Annual Meeting of the Chemical Society of Japan.
55. Palladium-Catalyzed Cross-Coupling of Benzylic Carbonates with Organotin Compounds
Masato Ohsumi, Ryoichi Kuwano
88th Annual Meeting of the Chemical Society of Japan.
56. Palladium-Catalyzed Asymmetric Benzylation of Active Methine Compounds
Daisuke Doyama, Ryoichi Kuwano
88th Annual Meeting of the Chemical Society of Japan.
57. Palladium-Catalyzed Cross-Coupling of Bis(o-substituted aryl)amines with aryl halides
Yasuhiro Matsumoto, Takenori Shige, Shinichi Soga, Yasuaki Soga, Ryoichi Kuwano
88th Annual Meeting of the Chemical Society of Japan.
58. Novel Transformations of Benzylic Esters Using Transition-Metal Catalysis
Ryoichi Kuwano.
59. Transformations of benzylic esters using palladium catalysis
Ryoichi Kuwano
International Symposium of Molecular Science 2008.
60. Catalytic Asymmetric Hydrogenation of Pyrroles.
61. Catalytic Asymmetric Hydrogenation of Aromatic Compounds
Ryoichi Kuwano
The 3rd PKNU-KU Joint Symposium on Sciences, Progress in Methematics, Physics, and Chemistry.
62. Catalytic Asymmetric Benzylation of Active Methine Compounds
Ryoichi Kuwano, Masashi Yokogi.
63. Catalytic Asymmetric Benzylation of Active Methine Compounds
Doyama Daisuke, Ryoichi Kuwano.
64. Ruthenium-Catalyzed Asymmetric Hydrogenation of Naphthalenes
Ryuichi Morioka, Manabu Kashiwabara, Ryoichi Kuwano
87th Annual Meeting of the Chemical Society of Japan.
65. Catalytic Asymmetric Hydrogenation of Benzene Ring in Quinolines
Kazuki Hirasata, Ryoichi Kuwano
87th Annual Meeting of the Chemical Society of Japan.
66. Catalytic Asymmetric Hydrogenation of Pyrrole
Manabu Kashiwabara, Ryoichi Kuwano
87th Annual Meeting of the Chemical Society of Japan.
67. Iridium-Catalyzed Benzylic Alkylation of Benzylic Carbonates
Azusa Yamamoto, Ryoichi Kuwano
87th Annual Meeting of the Chemical Society of Japan.
68. Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Diarylmethyl Carbonates with Arylboronic Acids
Jung-Yi Yu, Ryoichi Kuwano
87th Annual Meeting of the Chemical Society of Japan.
69. Palladium-Catalyzed Nucleophilic Substitution of Benzylic Acetates
Ryoichi Kuwano, Masashi Yokogi
87th Annual Meeting of the Chemical Society of Japan.
70. Highly Active Palladium Catalyst for Nucleophilic Substitution of Benzylic Carbonates
Masashi Yokogi, Ryoichi Kuwano
87th Annual Meeting of the Chemical Society of Japan.
71. Transition-Metal-Catalyzed Nucleophilic Substitution of Benzylic Esters
Ryoichi Kuwano
The 2nd KU-PKNU Joint Symposium on Sciences, Progress in Physics and Chemistry.
72. Ruthenium-Catalyzed Asymmetric Hydrogenation of Indoles
Ryoichi Kuwano, Manabu Kashiwabara.
73. Palladium-Catalyzed Benzylic Substitution of alpha-Branched Benzylic Esters
Hiroki Kusano, Ryoichi Kuwano.
74. Palladium-Catalyzed Cycloaddition of Orthoquinodimethanes with Dienophiles
Takenori Shige, Ryoichi Kuwano.
75. A New Access to Optically Active Heterocycles: Catalytic Asymmetric Hydrogenation of Heteroaromatics
Ryoichi Kuwano
The 23rd Seminar on Synthetic Organic Chemistry.
76. Palladium-Catalyzed Formal [4+2] Cycloaddtion of o-Xylylenes with Dienophiles
Ryoichi Kuwano, Takenori Shige
50th Symposium on Organometallic Chemistry, Japan.
77. Transition-Metal-Catalyzed Nucleophilic Substitution of benzylic Esters.
78. Cross-Coupling of Benzylic Acetates with Arylboronic Acids
Masashi Yokogi, Ryoichi Kuwano
86th Annual Meeting of the Chemical Society of Japan.
79. Palladium-Catalyzed Benzylic Alkylation of Diphenylmethyl Esters
Hiroki Kusano, Ryoichi Kuwano
86th Annual Meeting of the Chemical Society of Japan.
80. Generation of an o-quinodimethane equivalent from o-(silylmethyl)benzyl ester mediated by a palladium catalyst and its [4+2] cycloaddition with olefins
Takinori Shige, Ryoichi Kuwano
86th Annual Meeting of the Chemical Society of Japan.
81. Enantioselective Hydrogenation of 3-Substituted N-Boc-Indole Catalyzed by a Chiral Ruthenium
Manabu Kashiwabara, Yasuhiro Ueda, Ryoichi Kuwano
86th Annual Meeting of the Chemical Society of Japan.
82. Synthesis of N-Chiral Amines Catalyzed by a Palladium Complex
Tsuyoshi Shirahama, Ryoichi Kuwano
86th Annual Meeting of the Chemical Society of Japan.
83. Catalytic Asymmetric Hydrogenation of Heteroaromatics, Indoles
Ryoichi Kuwano
Pacifichem 2005.
84. A new class of substrate for palladium-catalyzed reactions: benzylic esters
Ryoichi Kuwano.
85. Palladium-Catalyzed Benzylic Sulfonylation of Benzyl Carbonates
Yutaka Kondo, Ryoichi Kuwano
85th Annual Meeting of the Chemical Society of Japan.
86. A Facial Generation of o-Quinodimethane from 2-[(Trimethylsillyl)- methyl]benzyl Acetate and Its Application to [4+2] Cycloaddition
Takenori Shige, Ryoichi Kuwano
85th Annual Meeting of the Chemical Society of Japan.
87. Cross-Coupling of Benzylic Carbonates with Arylboronic Acids
Masashi Yokogi, Ryoichi Kuwano
85th Annual Meeting of the Chemical Society of Japan.
88. Enantioselective Hydrogenation of N-Boc-indole Catalyzed by Chiral Ruthenium Complex
Manabu Kashiwabara, Ryoichi Kuwano
85th Annual Meeting of the Chemical Society of Japan.
89. Highly Enantioselective Hydrogenation of 3-Substituted Indoles
Kohei Kaneda, Takashi Ito, Koji Sato, Yoshihiko ito, Ryoichi Kuwano
84th Annual Meeting of the Chemical Society of Japan.
90. Highly Enantioselective Hydrogenation of 3-Substituted Indoles
Kohei Kaneda, Takashi Ito, Koji Sato, Yoshihiko ito, Ryoichi Kuwano
84th Annual Meeting of the Chemical Society of Japan.
91. Palladium-Catalyzed Benzylic Substitutions of Benzylic Esters
Ryoichi Kuwano, Yutaka Kondo, Yosuke Matsuyama
IKCOC-9.
92. Catalytic Asymmetric Hydrogenation of Indoles
Ryoichi Kuwano, Yutaka Kondo, Yosuke Matsuyama
50th Symposium on Organometallic Chemistry, Japan.
93. A New Aspect of Organic Synthesis by means of Palladium Complex
Ryoichi Kuwano.
94. Palladium-Catalyzed Asymmetric Decarboxylation-Allylation Reaction of Allyl beta-Keto-alpha-aminocarboxylates
Naoki Ishida, Ryoichi Kuwano, Yoshihiko Ito
83th Annual Meeting of the Chemical Society of Japan.
95. Asymmetric Allylation of 1,3-Diketones Catalyzed by BINAP-Pd Complex and the Mechanism of Asymmetric Induction
Ryoichi Kuwano, Kei-ichi Uchida, Yoshihiko Ito
83th Annual Meeting of the Chemical Society of Japan.
96. Palladium-Catalyzed Benzylic Alkylation
Yutaka Kondo, Ryoichi Kuwano
83th Annual Meeting of the Chemical Society of Japan.
97. Catalytic Asymmetric Hydrogenation of Unsaturated Heterocycles
Ryoichi Kuwano.
98. Catalytic Asymmetric Allylation of 1,3-Diketones
Ryoichi Kuwano, Ryo Nishio, Yoshihiko Ito
78th Annual Meeting of the Chemical Society of Japan.
99. Catalytic Asymmetric Hydorogenation of Heteroaromatic Compounds, 2-Substituted Indoles
Ryoichi Kuwano, Koji Sato, Takashi Kurokawa, Daisuke Karube, Yoshihiko Ito
78th Annual Meeting of the Chemical Society of Japan.
100. Hydrogenation of 5-Membered Heteroaromatic Compounds Catalyzed by a Rhodium Complex
Ryoichi Kuwano, Koji Sato, Yoshihiko Ito
78th Annual Meeting of the Chemical Society of Japan.
101. Catalytic Allylation of Prochiral Nucleophiles
Ryoichi Kuwano, Ryo Nishio, Yoshihiko Ito
77th Annual Meeting of the Chemical Society of Japan.
102. Catalytic Asymmetric Allylation of alpha-Acetamido-beta-ketophosphonates
Ryoichi Kuwano, Ryo Nishio, Yoshihiko Ito
76th Annual Meeting of the Chemical Society of Japan.
103. Highly Enantioselective Allylation of Prochiral Nucleophiles: alpha-Acetamido-beta-ketoesters
Ryoichi Kuwano, Yoshihiko Ito
76th Annual Meeting of the Chemical Society of Japan.
104. Asymmetric Hydrogenation of Cyclic Enamides Catalyzed by Chiral Rhodium Complexes: Competitive Mechanisms Depending upon P-Substituents of Chiral Diphosphines
Ryoichi Kuwano, Daisuke Karube, and Yoshihiko Ito
45th Symposium on Organometallic Chemistry, Japan.
105. catalytic Asymmetric Hydrogenation of alpha,beta-Bis(N-acylamino)acrylates
Ryoichi Kuwano, Satoshi Okuda, Yoshihiko Ito
74th Annual Meeting of the Chemical Society of Japan.
106. Catalytic Asymmetric Hydrogenation of 1,4,5,6-Tetrahydropyrazine-2-carboxamides
Ryoichi Kuwano, Yoshihiko Ito
74th Annual Meeting of the Chemical Society of Japan.
107. Catalytic Asymmetric Hydrogenation of Cyclic Enamides with TRAP-Rh Complex
Ryoichi Kuwano, Daisuke karube, Yoshihiko Ito
74th Annual Meeting of the Chemical Society of Japan.