pi-electron materials open up a new horizon for catalytic reactions

• Project/Area Number: 18K14209
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: The University of Tokyo
• Principal Investigator: Kitanosono Taku 東京大学, 大学院理学系研究科(理学部), 助教 (50755981)
• Project Period (FY): 2018-04-01 – 2020-03-31
• Project Status: Completed (Fiscal Year 2019)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2019: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2018: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: π電子材料 / Lewis酸 / 水中反応 / 界面活性剤 / 不斉反応場

Outline of Final Research Achievements

Single-walled carbon nanotubes (SWNTs) were demonstrated to render simple nickel catalysts effective in water. Integration of the nickel ions with chiral ligands and surfactants at the nanotube surface produces a highly enantioselective catalyst for nitrone formation from aldoximes and unsaturated ketones with long-term stability. Spectroscopy suggested that SWNTs enhanced electron density at the nickel center as well as provided a hydrophobic milieu.

Academic Significance and Societal Importance of the Research Achievements

本研究成果は、近年水中で展開されてきた有機化学に新たな領域を切り拓くと同時に、カーボンナノチューブの新たな活用法を提示するものである。また反応媒体として水を活用することで、均一系触媒や有機溶媒中では達成できない精密な触媒的不斉合成発展へ繋がることが期待される。

Research Products

• [Journal Article] Reactions in Water Involving the “On‐Water” Mechanism (2020)
  • Author(s): Kitanosono Taku、Kobayashi Shu
  • Journal Title: Chem. Eur. J. Volume: - Issue: 43 Pages: 9408-9429
  • DOI: 10.1002/chem.201905482
  • Peer Reviewed
• [Journal Article] Chiral Lewis acids integrated with single-walled carbon nanotubes for asymmetric catalysis in water (2018)
  • Author(s): T. Kitanosono, P. Xu, S. Kobayashi
  • Journal Title: Science Volume: 362 Issue: 6412 Pages: 311-315
  • DOI: 10.1126/science.aap7883
  • Peer Reviewed
• [Presentation] Application of Chiral Lewis Acids Integrated with Single-Walled Carbon Nanotubes in Water (2020)
  • Author(s): Taku Kitanosono, Shu Kobayashi
  • Organizer: 日本化学会第100春季年会
• [Presentation] Chiral Lewis Acids integrated with Single-Walled Carbon Nanotubes in Water (2019)
  • Author(s): Taku Kitanosono, Pengyu Xu, Shu Kobayashi
  • Organizer: 20th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 20)
  • Int'l Joint Research
• [Presentation] 水が拓く金属-カーボンナノチューブ触媒のニューワールド (2019)
  • Author(s): 北之園拓
  • Organizer: 第9回CSJ化学フェスタ2019
  • Invited
• [Presentation] 水中で効果的に機能するキラルルイス酸-単層カーボンナノチューブ複合触媒の開発 (2019)
  • Author(s): 北之園拓・小林修
  • Organizer: 創造機能化学第116委員会 合同分科会
• [Presentation] Chiral Lewis Acids integrated with Single-Walled Carbon Nanotubes in Water (2019)
  • Author(s): T. Kitanosono, P. Xu, S. Kobayashi
  • Organizer: 日本化学会第99春季年会
• [Presentation] Evaluation of Single-Walled Carbon Nanotubes for Integration with Chiral Lewis acid-surfactant-combined Catalysts (2019)
  • Author(s): J. Bahri, T. Kitanosono, S. Kobayashi
  • Organizer: 日本化学会第99春季年会
• [Presentation] 水中で効果的に機能するキラルルイス酸-単層カーボンナノチューブ複合触媒の開発 (2018)
  • Author(s): 北之園拓・徐鵬宇・小林修
  • Organizer: 第113回有機合成シンポジウム
• [Presentation] Chiral Lewis Acids Integrated with Single-Walled Carbon Nanotubes for Asymmetric Catalysis in Water (2018)
  • Author(s): T. Kitanosono, P. Xu, S. Kobayashi
  • Organizer: Young Generation Meeting with Professor Nicolaou-Symposium
  • Int'l Joint Research
• [Book] Science of Synthesis: Advances in Organoboron Chemistry towards Organic Synthesis (2020)
  • Author(s): Taku Kitanosono, Shu Kobayashi
  • Total Pages: 574
  • Publisher: Thieme Chemistry
  • ISBN: 9783132429710
• [Book] Japanese Scientists in Science 2018 - サイエンス誌に載った日本人研究者 - (2019)
  • Author(s): Science Japan Customer Service Office編輯
  • Total Pages: 71
  • Publisher: American Association for the Advancement of Science (AAAS)
• [Remarks] カーボンナノチューブの新展開：水中で働く不斉触媒の高機能化を実現
  • URL: https://www.s.u-tokyo.ac.jp/ja/press/2018/6097/