The development of catalytic cross-couplings using anisole derivatives

• Project/Area Number: 21750100
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Osaka University
• Principal Investigator: TOBISU Mamoru 大阪大学, 工学研究科, 特任講師(常勤) (60403143)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2009: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 均一系触媒 / 遷移金属錯体 / 不活性結合切断 / 炭素-酸素結合切断 / ニッケル触媒 / 還元的切断 / ヒドロシラン / アミノ化 / アニソール / クロスカップリング

Research Abstract

Inert phenol derivatives, such as anisole, can be employed as an aryl halide surrogate. The key to success is the combined use of a nickel catalyst and bulky and electron-rich ligands. The Suzuki-Miyaura type reaction using organoboron reagents, amination using secondary amines, and reductive cleavage using hydrosilane have been developed.

Research Products

• [Journal Article] Nickel-Catalyzed Reductive Cleavage of Aryl- Oxygen Bonds in Alkoxy- and Pivaloxyarenes Using Hydrosilane as a Mild Reducing Agent (2011)
  • Author(s): Mamoru Tobisu, Ken Yamakawa, Toshiaki Shimasaki, and Naoto Chatani
  • Journal Title: Chemical Communications Volume: 47巻 Pages: 2946-2948
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Reductive Cleavage of Aryl□Oxygen Bonds in Alkoxy- and Pivaloxyarenes Using Hydrosilane as a Mild Reducing Agent (2011)
  • Author(s): Mamoru Tobisu, Ken Yamakawa, Toshiaki Shimasaki, Naoto Chatani
  • Journal Title: Chemical Communications Volume: 47 Pages: 2946-2948
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Amination of Aryl Pivalates via the Cleavage of Aryl-Oxygen Bonds (2010)
  • Author(s): Toshiaki Shimasaki, Mamoru Tobisu, and Naoto Chatani
  • Journal Title: Angewandte Chemie, International Edition in English Volume: 49巻 Pages: 2929-2932
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Amination of Aryl Carboxylates via the Cleavage of Aryl-Oxygen Bonds (2010)
  • Author(s): Toshiaki Shimasaki, Mamoru Tobisu, Naoto Chatani
  • Journal Title: Angewandte Chemie, International Edition in English Volume: 49 Pages: 2929-2932
  • Peer Reviewed
• [Journal Article] Ni^0-catalyzed Direct Amination of Anisoles Involving the Cleavage of Carbon-Oxygen Bonds (2009)
  • Author(s): Mamoru Tobisu, Toshiaki Shimasaki and Naoto Chatani
  • Journal Title: Chemistry Letters Volume: 38巻 Pages: 710-711
  • NAID: 10025124262
  • Peer Reviewed
• [Journal Article] Ni^0-catalyzed Direct Amination of Anisoles Involving the Cleavage of Carbon-Oxygen Bonds (2009)
  • Author(s): Mamoru Tobisu, Toshiaki Shimasaki, Naoto Chatani
  • Journal Title: Chemistry Letters Volume: 38 Pages: 710-711
  • NAID: 10025124262
  • Peer Reviewed