Development of Efficient Catalytic Processes toward Functional Molecules Synthesis

• Project/Area Number: 20350045
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Nagoya University (2009-2010); Tokyo Institute of Technology (2008)
• Principal Investigator: YAMAMOTO Yoshihiko 名古屋大学, 工学研究科, 准教授 (60283412)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥19,110,000 (Direct Cost: ¥14,700,000、Indirect Cost: ¥4,410,000); Fiscal Year 2010: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2009: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2008: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
• Keywords: 多成分カップリングプロセス / ルテニウム触媒 / パラジウム触媒 / 銅触媒 / カップリング反応 / 環化付加反応 / アルコキシカルボニル化反応 / ボロン酸 / 生理活性化合物 / ヒドロアリール化 / クマリン / モリブデン錯体触媒 / フリーデル・クラフツ反応 / 芳香族化合物 / ブレンステッド酸触媒 / クロマン

Research Abstract

Novel transition-metal-catalyzed coupling processes have been developed and they have been applied to the concise syntheses of biologically active compounds. These studies include the ruthenium-catalyzed cyclizations of diynes, the copper-catalyzed hydroarylations of electron-deficient alkynes, the palladium-catalyzed alkoxycarbonylation of arylboronates, etc. and the constructions of molecular framworks of natural products and drugs have been achieved using these processes.

Research Products

• [Journal Article] Copper-Catalyzed Regio-and Stereoselective Conjugate Allylation of Electron-Deficient Alkynes with Allylboronates under Mild Conditions (2012)
  • Author(s): Yoshihiko Yamamoto, Satoshi Yamada, Hisao Nishiyama
  • Journal Title: Chem. Eur. J. Volume: 18(11) Issue: 11 Pages: 3153-3156
  • DOI: 10.1002/chem.201103697
  • Peer Reviewed
• [Journal Article] Ruthenium-catalyzed cyclization/transfer hydrogenation of 1,6-diynes : unprecedented mode of alcohol activation via metallacyclopentatriene (2011)
  • Author(s): Yamashita, K.; Nagashima, Y.; Yamamoto, Y.; Nishiyama, H.
  • Journal Title: Chemical Communications Volume: 47 Issue: 41 Pages: 11552-11554
  • DOI: 10.1039/c1cc13744a
  • Peer Reviewed
• [Journal Article] Synthesis of 3-Arylindole-2-carboxylates via Copper-Catalyzed Hydroarylation of o-Nitrophenyl-Substituted Alkynoates and Subsequent Cadogan Cyclization (2011)
  • Author(s): Yoshihiko Yamamoto, Satoshi Yamada, Hisao Nishiyama
  • Journal Title: Adv. Synth. Catal. Volume: 353(5) Issue: 5 Pages: 701-706
  • DOI: 10.1002/adsc.201000858
  • Peer Reviewed
• [Journal Article] Activation of a water molecule under mild conditions by ruthenacyclopentatriene : Mechanism of hydrative cyclization of diynes (2011)
  • Author(s): Yoshihiko Yamamoto, Ken Yamashita, Hisao Nishiyama
  • Journal Title: Chem. Commun. Volume: 47(5) Issue: 5 Pages: 1556-1558
  • DOI: 10.1039/c0cc04345a
  • Peer Reviewed
• [Journal Article] Systematic Evaluation of Substituted Cyclopentadienyl Ruthenium Complexes, [(η^5-C_5Me_nH_<5-n>) RuCl(cod)], for Catalytic Cycloadditions of Diynes (2010)
  • Author(s): Yoshihiko Yamamoto, Ken Yamashita, Yu Harada
  • Journal Title: An Asian Journal Volume: 5巻, 4号 Issue: 4 Pages: 946-952
  • DOI: 10.1002/asia.200900531
  • Peer Reviewed
• [Journal Article] Synthesis of Organometallic Analogues of Spirocyclic C-Arylribosides (2010)
  • Author(s): Yoshihiko Yamamoto, Ken Yamashita, Mitsutaka Nakamura
  • Journal Title: Organometallics Volume: 29巻, 6号 Issue: 6 Pages: 1472-1478
  • DOI: 10.1021/om100043f
  • Peer Reviewed
• [Journal Article] The First General and Selective Palladium(II)-Catalyzed Alkoxycarbonylation of Arylboronates : Interplay among Benzoquinone-Ligated Palladium(0) Complex, Organoboron, and Alcohol Solvent (2010)
  • Author(s): Yoshihiko Yamamoto
  • Journal Title: Advanced Synthesis & Catalysis Volume: 352巻, 2-3号 Issue: 2-3 Pages: 478-492
  • DOI: 10.1002/adsc.200900836
  • Peer Reviewed
• [Journal Article] SYNTHESIS OF 4-ARYL-SUBSTITUTED BUTENOLIDES AND PENTENOLIDES BY COPPER-CATALYZED HYDROARYLATION (2010)
  • Author(s): Yoshihiko Yamamoto, Naohiro Kirai
  • Journal Title: Heterocycles Volume: 80巻, 1号 Issue: 21 Pages: 269-279
  • DOI: 10.1002/chin.201021133
  • NAID: 40016900104
  • Peer Reviewed
• [Journal Article] Systematic Evaluation of Substituted Cyclopentadienyl Ruthenium Complexes, [(η^5-C_5Me_nH_<5-n>RuCl(cod)], for Catalytic Cycloadditions of Diynes (2010)
  • Author(s): Yoshihiko Yamamoto, Ken Yamashita, Yu Harada
  • Journal Title: Chemistry-An Asian Journal Volume: 5 Pages: 946-952
  • Peer Reviewed
• [Journal Article] Systematic Evaluation of Substituted Cyclopentadienyl Ruthenium Complexes, [(η^5-C_5Me_nH_<5-n>)RuCl(cod)], for Catalytic Cycloadditions of Diynes (2010)
  • Author(s): Yoshihiko Yamamoto, Ken Yamashita, Yu Harada
  • Journal Title: Chemistry-An Asian Journal Volume: 5巻 Pages: 946-952
  • Peer Reviewed
• [Journal Article] Copper-Catalyzed Stereoselective Hydroarylation of 3-Aryl-2-propynenitriles with Arylboronic Acids (2009)
  • Author(s): Yoshihiko Yamamoto, Tsuyoshi Asatani, Naohiro Kirai
  • Journal Title: Advanced Synthesis & Catalysis Volume: 351巻, 9号 Issue: 9 Pages: 1243-1249
  • DOI: 10.1002/adsc.200900067
  • Peer Reviewed
• [Journal Article] Synthesis of 2, 5-Dihydrofuran-fused Quinones from Ether-Tethered Diiododiyne (2009)
  • Author(s): Yoshihiko Yamamoto, Ryosuke Takuma, Tomitaka Hotta, and Ken Yamashita
  • Journal Title: The Journal of Organic Chemistry Volume: 74巻, 11号 Issue: 11 Pages: 4324-4328
  • DOI: 10.1021/jo9005975
  • Peer Reviewed
• [Journal Article] Synthesis of Chromans via [3 + 3] Cyclocoupling of Phenols with Allylic Alcohols Using a Mo/o-Chloranil Catalyst System (2009)
  • Author(s): Y. Yamamoto, K. Itonaga
  • Journal Title: Organic Letters 11 Pages: 717-720
  • Peer Reviewed
• [Journal Article] Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates (2008)
  • Author(s): Y. Yamamoto, N. Kirai, Y. Harada
  • Journal Title: Chemical Communications Pages: 2010-2012
  • Peer Reviewed
• [Journal Article] Versatile Friedel-Crafts-Type Alkylation of Benzene Derivatives Using a Molybdenum Complex/ortho-Chloranil Catalytic System (2008)
  • Author(s): Y. Yamamoto, K. Itonaga
  • Journal Title: Chemistry-A European Journal 14 Pages: 10705-10715
  • Peer Reviewed
• [Journal Article] Synthesis of 4-Arylcoumarins via Cu-catalyzed Hydroarylation with Arylboronic Acids (2008)
  • Author(s): Y. Yamamoto, N. Kirai
  • Journal Title: Organic Letters 10 Pages: 5513-5516
  • Peer Reviewed
• [Journal Article] Silver-Catalyzed Csp-H and Csp-Si Bond Transformations and Related Processes (2008)
  • Author(s): Y. Yamamoto
  • Journal Title: Chemical Reviews 108 Pages: 3199-3222
  • Peer Reviewed
• [Journal Article] ルテニウム触媒環化三量化反応を用いるC-アリールグリコシドの合成 (2008)
  • Author(s): Y. Yamamoto
  • Journal Title: 有機合成化学協会誌 66 Pages: 795-805
  • NAID: 10024278434
  • Peer Reviewed
• [Presentation] ルテニウム触媒とハンチュエステルを用いたジインの水素移動型還元環化反応 (2012)
  • Author(s): 森翔大,山下健,山本芳彦,西山久雄
  • Organizer: 日本化学会第92回春季年会
  • Place of Presentation: 慶應大学矢上キャンパス,神奈川県
• [Presentation] ルテニウム触媒を用いた酸素移動型[2+2+1]環化による1, 6-ジインからのフラン新規合成法 (2012)
  • Author(s): 山下健,山本芳彦,西山久雄
  • Organizer: 日本化学会第92回春季年会
  • Place of Presentation: 慶應大学矢上キャンパス,神奈川県
• [Presentation] ルテニウム環状ビスカルベン錯体と酸素求核剤の反応性 (2010)
  • Author(s): 山下健, 山本芳彦, 西山久雄
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 中央大学多摩キャンパス(東京)
  • Year and Date: 2010-09-17
• [Presentation] 環状ルテニウムビスカルベン錯体と水の直接的反応 (2010)
  • Author(s): 山下健, 山本芳彦, 西山久雄
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学本部キャンパス(東大阪)
  • Year and Date: 2010-03-29
• [Presentation] ルテニウム環状ビスカルベン錯体と酸素求核剤の反応性 (2010)
  • Author(s): 山下健,山本芳彦,西山久雄
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 中央大学多摩キャンパス,東京都
• [Presentation] 銅触媒ヒドロアリール化反応を用いる含窒素複素環化合物の合成 (2010)
  • Author(s): 山田諭,山本芳彦,西山久雄
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学本部キャンパス,大阪府
• [Presentation] 環状ルテニウムビスカルベン錯体と水の直接的反応 (2010)
  • Author(s): 山下健,山本芳彦,西山久雄
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 近畿大学本部キャンパス,大阪府
• [Presentation] Cu-Catalyzed Selective Hydroarylation of Electron-Deficient Alkynes with Arylboronic Acids (2009)
  • Author(s): Yoshihiko Yamamoto
  • Organizer: International Symposium on Organic Synthesis 2009
  • Place of Presentation: 韓国釜山
  • Year and Date: 2009-01-19
• [Presentation] Improved Cp' RuCl Catalysts for[2+2+2] Cycloaddition of Alkynes (2009)
  • Author(s): Ken Yamashita, Yoshihiko Yamamoto, Hisao Nishiyama
  • Organizer: International Symposium on Catalysis and Fine Chemicals 2009
  • Place of Presentation: Korea University, Seoul, Korea
• [Presentation] Improved Ru(II) Catalysts for Alkyne[2+2+2] Cycloaddition and Expansion of Their Utility in Organic Synthesis (2009)
  • Author(s): Ken Yamashita, Yoshihiko Yamamoto, Hisao Nishiyama
  • Organizer: The 11th International Kyoto Conference on New Aspects of Organic Chemistry
  • Place of Presentation: Rihga Royal Hetel Kyoto, Japan
• [Presentation] Cp' RuCl(cod)錯体触媒における立体・電子効果の解明 (2009)
  • Author(s): 山下健,山本芳彦,西山久雄
  • Organizer: 第56回有機金属化学討論会
  • Place of Presentation: 同志社大学今出川キャンパス,京都府
• [Presentation] Cu-Catalyzed Hydroarylation of Electron-Deficient Alkynes (2008)
  • Author(s): 山本芳彦
  • Organizer: 光利用プロジェクト有機合成化学シンポジウム
  • Place of Presentation: 九州大学筑紫地区
  • Year and Date: 2008-12-20
• [Presentation] 遷移金属錯体と酸化剤・溶媒の協奏作用に基づく触媒プロセス (2008)
  • Author(s): 山本芳彦
  • Organizer: 特定領域研究「協奏機能触媒」第5回公開シンポジウム
  • Place of Presentation: 大阪大学基礎工学部国際棟
  • Year and Date: 2008-12-03
• [Presentation] Cu-catalyzed Stereoselective Conjugate Addition of Arylboronic Acids to Alkynoates (2008)
  • Author(s): N. Kirai, Y. Yamamoto
  • Organizer: 6^<th> Workshop on Organic Chemistry for Junior Chemists
  • Place of Presentation: 東京工業大学
  • Year and Date: 2008-11-03
• [Presentation] 遷移金属触媒を活用する芳香族化合物の精密合成 (2008)
  • Author(s): 山本芳彦
  • Organizer: 特定領域研究「元素相乗系の化学」第4回公開若手コロキウム
  • Place of Presentation: 北海道グリーンピア大沼
  • Year and Date: 2008-09-04
• [Book] 第4編均一系触媒、第11章環化反応、触媒調製ハンドブック (2011)
  • Author(s): 山本芳彦
  • Publisher: (株)エヌ・ティー・エス
• [Remarks] Naohiro Kirai, Yoshihiko Yamamoto, STEREOSELECTIVE SYNTHESIS OF 3-ARYLACRYLATES BY COPPER-CATALYZED SYN HYDROARYLATION[(E)-Methyl 3-phenyloct-2-enoate], Organic Syntheses, 87巻, 2009, 53-58.
• [Remarks] Yoshihiko Yamamoto, Chloro[(1, 2, 5, 6-η)-1, 5-cyclooctadiene][(1, 2, 3, 4, 5-η)-1, 2, 3, 4, 5-pentamethyl-2, 4-cyclopentadien-1-yl] ruthenium, Electronic Encyclopedia of Reagents for Organic Synthesis, Wiley, 2009.