Utilization of simple reagents for leading-edge synthetic reactions

• Project/Area Number: 20245010
• Research Category: Grant-in-Aid for Scientific Research (A)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kyushu University
• Principal Investigator: TOKUNAGA Makoto Kyushu University, 大学院・理学研究院, 教授 (40301767)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥18,980,000 (Direct Cost: ¥14,600,000、Indirect Cost: ¥4,380,000); Fiscal Year 2010: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000); Fiscal Year 2009: ¥11,440,000 (Direct Cost: ¥8,800,000、Indirect Cost: ¥2,640,000)
• Keywords: 単純反応剤 / 水素 / 酸素 / 水 / 一酸化炭素 / 原子効率 / 触媒 / ヒドロホルミル化 / フィッシャートロプシュ反応 / 反ASF反応 / 酸化物担持金ナノ粒子 / 水和 / ヒドロアルコキシ化 / 環化カルボニル化 / インドリノン誘導体 / 酸化コバルト担持金ナノ粒子 / 合成ガス / 固体触媒 / 酸化物担持金ナノ粒子触媒 / 水素スピルオーバー / 0価金属 / Pauson-Khan反応 / Fischer-Tropsch反応 / anti-ASF分布 / 炭化水素

Research Abstract

As for the utilization of oxygen nucleophiles, the development of hydroalkoxykation of olefins, asymmetric alcohokysis of vinyl ethers, asymmetric hydrolysis of esters, irreversible hydrolysis of esters have been achieved. Carbon monoxide utilization for hydroformykation, Fischer-Tropsch reaction etc. were also achieved.

Research Products

• [Journal Article] Irreversible Catalytic Ester Hydrolysis of Allyl Esters to Give Acids and Aldehydes by Homogeneous Ruthenium and Ruthenium/Palladium Dual Catalyst Systems. (2011)
  • Author(s): Nakamura A., Hamasaki A., Goto S., Utsunomiya M., Tokunaga M.
  • Journal Title: Adv.Synth.Catal. 353 Pages: 973-984
  • Peer Reviewed
• [Journal Article] Controllable Fischer-Tropsch Synthesis by in situ Produced 1-Olefins. (2010)
  • Author(s): Liu X., Tokunaga M.
  • Journal Title: ChemCatChem. 2 Pages: 1569-1572
  • Peer Reviewed
• [Journal Article] Highly Atom Efficient Catalytic Reactions Utilizing Water and Alcohols as Reagents. (2010)
  • Author(s): Hamasaki A.; Yamamoto E.; Ito H, Tokunaga M.
  • Journal Title: J.Organomet. Chem 696 Pages: 202-210
  • Peer Reviewed
• [Journal Article] 金属錯体触媒による加水分解、加アルコール分解およびアルコールの付加反応 (2010)
  • Author(s): 徳永信、濱崎昭行、山本英治、伊藤寿
  • Journal Title: 磯含滅危学赫会諾 68 Pages: 738-744
  • NAID: 10026869968
  • Peer Reviewed
• [Journal Article] Highly Atom Efficient Catalytic Reactions Utilizing Water and Alcohols as Regents (2010)
  • Author(s): Hamasaki, A.; Yamamoto, E.; Ito, H.; Tokunaga, M.
  • Journal Title: J.Olganomet.Chem Volume: 696 Pages: 202-210
  • Peer Reviewed
• [Journal Article] 金属錯体触媒による加水分解、加アルコール分解およびアルコールの付加反応 (2010)
  • Author(s): 徳永信、濱崎昭行、山本英治、伊藤寿
  • Journal Title: 有機合成化学協会誌 Volume: 68 Pages: 738-744
  • NAID: 10026869968
  • Peer Reviewed
• [Journal Article] Enhancement of Reaction Effciency by Functionalyzed Alcohols on Gold(I)Catalyzed Intermolecular Hydroalkoxylation of Unactivated Olefins. (2009)
  • Author(s): Hirai T.; Hamasaki A.;, Nakamura A.; Tokunaga M.
  • Journal Title: Org.Lett 11
  • Peer Reviewed
• [Journal Article] One-Pot Synthesis of Indoles and Aniline Derivatives from Nitroarenes under Hydrogenation Condition with Supported Gold Nanoparticles (2009)
  • Author(s): Yamane, Y, Liu, X., Hamasaki A., Ishida, T., Hamta, M., Yokoyama, T., Tokunaga M.
  • Journal Title: Org.Lett. 11 Pages: 5162-5165
  • Peer Reviewed
• [Journal Article] Hydrofbrmylation of Olefins by Au/Co_3O_4 Catalysts (2009)
  • Author(s): Liu, X., Hu, B., Fujimoto, K., Hamta, M., Tokunaga M.
  • Journal Title: Appl.Catal.B 92 Pages: 411-421
  • Peer Reviewed
• [Journal Article] Kinetic Resolution of P-Chirogenic Compounds by Pd-catalyzed Alcoholysis of Vinyl Ethers. (2009)
  • Author(s): Itoh, H., Yamamoto E., Masaoka, S., Sakai, K., Tokunaga M.
  • Journal Title: Adv.Synth.Catal. 351 Pages: 1796-1800
  • Peer Reviewed
• [Journal Article] Hydroformylation of Olefins by Au/Co_3O_4 Catalysts. (2009)
  • Author(s): Liu, X.; Hu, B.; Fujimoto, K.; Haruta, M.; Tokunaga, M.
  • Journal Title: Appl.Catal.B Volume: 92 Pages: 411-421
  • Peer Reviewed
• [Journal Article] Hydroformylation of Olefins by AU/Co_3O_4 Catalysts (2009)
  • Author(s): Liu, X., Hu, B., Fujimoto, K., Haruta, M., Tokunaga, M.
  • Journal Title: Appl.Catal.B 92 Pages: 411-421
  • Peer Reviewed
• [Journal Article] Amidocarbonylation of Aldehydes Utilizing Cobalt Oxide Supported-Gold Nanoparticles as a Heterogeneous Catalyst. (2008)
  • Author(s): Hamasaki A.; Liu X.; Tokunaga M.
  • Journal Title: Chem.Lett 37 Pages: 1292-1293
  • Peer Reviewed
• [Journal Article] Coprecipitated Gold-Tricobalt Tetraoxide Catalyst for Heterogeneous Hydroformylation of Olefins. (2008)
  • Author(s): Liu, X., Haruta, M., Tokunaga M.
  • Journal Title: Chem.Lett 37 Pages: 1290-1291
  • Peer Reviewed
• [Journal Article] Hydrolytic deallylation from N-allyl amides catalyzed by Pd(II) complexes. (2008)
  • Author(s): Ohmura N.; Nakamura A.; Hamasaki A.; Tokunaga M.
  • Journal Title: Eur.J.Org.Chem. Pages: 5042-5045
  • Peer Reviewed
• [Journal Article] Kinetic resolution of phosphoryl and sulfbnyl esters of 1,10-bi-2-naphthol via Pd-catalyzed alcoholysis of their vinyl ethers. (2008)
  • Author(s): Sakuma, T., Yamamoto E., Aoyama, H, Obora, Y, Tsuji, Y, Tokunaga M.
  • Journal Title: Tetrahedron : Asymmetry 19 Pages: 1593-1599
  • Peer Reviewed
• [Journal Article] Au(I) complexes-catalyzed transfbr vinylation of alcohols and carboxylic acids. (2008)
  • Author(s): Nakamura A., Tokunaga M.
  • Journal Title: Tetrahedron Lett. 49 Pages: 3729-3732
  • Peer Reviewed
• [Journal Article] Catalytic Asymmetric Hydrolysis : Asymmetric Hydrolytic Protonation of Enolesters Catalyzed by Phase Transfer Catalysts
  • Author(s): Yamamoto E., Nagai A. Hamasaki A. Tokunaga M.
  • Journal Title: Chem.Eur.J. in press.
  • Peer Reviewed
• [Journal Article] Anti-ASF distribution in Fischer-Tropsch Synthesis over Unsupported Cobalt Catalysts in a Batch Slurry Phase Reactor.
  • Author(s): Liu X., Hamasaki A., Honma T., Tokunaga M.
  • Journal Title: Catal.Today in press.
  • Peer Reviewed
• [Journal Article] Irreversible Catalytic Ester Hydrolysis of Allyl Esters to Give Acids and Aldehydes by Homogeneous Ruthenium and Ruthenium/Palladium Dual Catalyst Systems
  • Author(s): Nakamura, A.; Hamasaki, A; Goto, S.; Utsunomiya, M.; Tokunaga, M.
  • Journal Title: Adv.Synth.Catal Volume: (印刷中)
  • Peer Reviewed
• [Journal Article] Catalytic Asymmetric Hydrolysis : Asymmetric Hydrolytic Protonation of Enolesters Catalyzed by Phase Transfer Catalysts
  • Author(s): Yamamoto, E.; Nagai A.; Hamasaki, A.; Tokunaga, M.
  • Journal Title: Chem..Eur.J. Volume: (印刷中)
  • Peer Reviewed
• [Journal Article] Anti-ASF distribution in Fischer-Tropsch Synthesis over Unsupported Cobalt Catalysts in a Batch Slurry Phase Reactor
  • Author(s): Liu, X.; Hamasaki, A.; Honma, T.; Tokunaga, M.
  • Journal Title: Catal.Today Volume: (印刷中)
  • Peer Reviewed
• [Presentation] Supported gold nanoparticles-catalyzed one-pot synthesis of indoles and aniline derivatives from nitroarenes under hydrogenation condition (2010)
  • Author(s): Y.Yamane; X.Liu; A.Hamasaki; T.Ishida; M.Haruta; T.Yokoyama; M.tokunaga
  • Organizer: 2010環太平洋国際化学会議
  • Place of Presentation: ホノルル、アメリカ
  • Year and Date: 2010-12-19
• [Presentation] 酸化物担持金ナノ粒子触媒による合成反応 (2010)
  • Author(s): 徳永信
  • Organizer: 第43回有機金属若手の会/夏の学校2010
  • Place of Presentation: 福岡
  • Year and Date: 2010-07-06
• [Presentation] 金ナノ粒子触媒による有機合成反応の展開 (2010)
  • Author(s): 徳永信
  • Organizer: 統合物質創製化学推進事業第一回若手研究会
  • Place of Presentation: 福岡
  • Year and Date: 2010-06-12
• [Presentation] 酸化コバルト担持金ナノ粒子を触媒とした環化カルボニル化反応 (2010)
  • Author(s): 劉小浩・濱崎昭行・山根義弘・徳永信
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-26
• [Presentation] コバルト酸化物担持金ナノ粒子が触媒するオレフィンのヒドロアミノメチル化反応 (2009)
  • Author(s): 劉小浩・濱崎昭行・山根義弘・徳永信
  • Organizer: 第104回触媒討論会
  • Place of Presentation: 宮崎
  • Year and Date: 2009-09-30
• [Presentation] Ru/Pd触媒によるエステルの不可逆型加水分解反応、特定領域研究「協奏機能触媒」 (2009)
  • Author(s): 徳永信
  • Organizer: 第6回公開シンポジウム
  • Place of Presentation: 東京(東京大学武田先端知ビル)
  • Year and Date: 2009-04-25
• [Presentation] コバルトカルボニル錯体触媒を代替する金ナノ粒子と担体酸化物の協同効果 (2008)
  • Author(s): 徳永信
  • Organizer: Organometallic Seminar XXXVI
  • Place of Presentation: 福岡
  • Year and Date: 2008-12-16
• [Presentation] Hydrofbrmylation and Related Reactions Catalyzed by the Combination of Nanoparticles Au and Cobalt Oxide (2008)
  • Author(s): 徳永信
  • Organizer: 、Global COE Program : Prof.Jean-Marie Lehn Symposium III
  • Place of Presentation: 福岡
  • Year and Date: 2008-10-17
• [Presentation] 金ナノ粒子触媒による新しい有機合成反応 (2008)
  • Author(s): 徳永信
  • Organizer: 第24回若手化学者のための化学道場(徳島2008)
  • Place of Presentation: 徳島
  • Year and Date: 2008-09-11
• [Presentation] 酸化物担持金触媒による新しい有機合成反応、元素相乗系化合物の化学 (2008)
  • Author(s): 徳永信
  • Organizer: 第4回若手コロキウム
  • Place of Presentation: 北海道森町
  • Year and Date: 2008-09-04
• [Book] Chapter 6.20, Addition Reaction/Kinetic Resolution, Comprehensive Chirality(Vol 5 : Synthetic Methods IV-Synthetic Methods IV - Asymmetric Oxidation Reduction, C-N)( Maruoka, K., Yamamoto, H. Eds.)
  • Author(s): Tokunaga, M., Hamasaki, A.
  • Publisher: Elsevier, in press.
• [Book] Comprehensive Chirality/Chapter 6.20, Addition Reaction/Kinetic Resolution
  • Author(s): Tokunaga, M; Hamasaki, A.
  • Publisher: Elsevier(印刷中)
• [Patent(Industrial Property Rights)] エステルの不斉加水分解方法 (2011)
  • Inventor(s): 徳永信、濱崎昭行、山本英治、佐久間毅、大村直也、永井あやの、中村亮太
  • Industrial Property Rights Holder: 九州大学
  • Industrial Property Number: 2011-006529
  • Filing Date: 2011-01-16
• [Patent(Industrial Property Rights)] エステルの不斉加水分解方法 (2011)
  • Inventor(s): 徳永信、濱崎昭行、山本英治、大村直也、永井あやの、中村亮太
  • Industrial Property Rights Holder: 九州大学
  • Industrial Property Number: 2011-006529
  • Filing Date: 2011-01-16
• [Patent(Industrial Property Rights)] Tokunaga, M., Hamasaki, A. (2009)
  • Inventor(s): 徳永信、劉小浩、濱崎昭行、宇都宮賢、田中善幸
  • Industrial Property Rights Holder: 九州大学、三菱化学(株)
  • Patent Publication Number: 2009-241060
  • Filing Date: 2009-02-27
• [Patent(Industrial Property Rights)] カルボニル化合物の製造方法 (2008)
  • Inventor(s): 徳永信、中村麻美、宇都宮賢
  • Industrial Property Rights Holder: 九州大学、三菱化学(株)
  • Patent Publication Number: 2010-024171
  • Filing Date: 2008-07-17