Development of Environmentally Friendly Methods for Organic Synthesis based on Design and Preparation of Less Toxic Organotin Reagents

• Project/Area Number: 20550092
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Saitama University
• Principal Investigator: MIURA Katsukiyo Saitama University, 大学院・理工学研究科, 教授 (20251035)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000); Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2008: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 有機スズ反応剤 / 環境調和型反応 / ラジカル反応 / ヒドロスタンニル化 / ハロアルカン / ヒドロスタンナン / 環境調和型合成 / 還元反応 / 触媒反応 / 環境調合型合成

Research Abstract

Organotin reagents are valuable for fine organic synthesis. However, tributyltin compounds, frequently used for this purpose, have high toxicity with difficulty of decomposition and separation. To overcome these weaknesses, we studied synthesis and synthetic use of benzyltin compounds. Tribenzylstannane (Bn_3SnH) was found to be useful for radical reduction of organic halides. The tin byproducts (Bn_3SnX) are easily separable by filtration and silica gel column chromatography and decomposable by treatment with basic hydrogen peroxide.

Research Products

• [Journal Article] Indium Acetate-Catalyzed Intermolecular Radical Addition of Organic Iodides to Electron-Deficient Alkenes (2008)
  • Author(s): 三浦勝清、富田充、市川淳士、細見彰
  • Journal Title: 10巻 Pages: 133-136
  • Peer Reviewed
• [Journal Article] スタンニルラジカルを鍵中間体とする新規有機合成反応の開発 (2008)
  • Author(s): 三浦勝清
  • Journal Title: 有機合成化学協会誌 66巻 Pages: 17-27
  • NAID: 10020127473
  • Peer Reviewed
• [Journal Article] スタンニルラジカルを鍵中間体とする新規有機合成反応の開発 (2008)
  • Author(s): 三浦勝清
  • Journal Title: 有機合成化学協会誌 66 Pages: 17-27
  • NAID: 10020127473
  • Peer Reviewed
• [Journal Article] Indium(III) Acetate-Catalyzed Intermolecular Radical Addition of Organic Iodides to Electron-deficient Alkenes (2008)
  • Author(s): 三浦勝清
  • Journal Title: Organic Letters 10 Pages: 133-136
  • Peer Reviewed
• [Presentation] トリベンジルスタンナンを用いるハロアルカンやアルキンのラジカル反応 (2011)
  • Author(s): 山川健、木下英典、三浦勝清
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜・神奈川大学
  • Year and Date: 2011-03-29
• [Presentation] トリベンジルスズ化合物の合成と有機合成への利用 (2010)
  • Author(s): 山川健、木下英典、三浦勝清
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪・近畿大学
  • Year and Date: 2010-03-27
• [Remarks] ホームページ等
  • URL: http://www.apc.saitama-u.ac.jp/ygosei/san_pu_sheng_qing_yan_jiu_shi/top.html