Development of the catalyst featured by chemicallyπ-space for asymmetric Suzuki-Miyaura reaction

• Project/Area Number: 22750097
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Ryukoku University
• Principal Investigator: IWASAWA Tetsuo 龍谷大学, 理工学部, 准教授 (80452655)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000); Fiscal Year 2011: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2010: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
• Keywords: 不斉クロスカップリング / 軸不斉ビアリール / 不斉触媒 / 不斉ホスホナイト化合物

Research Abstract

Development of a catalyst that promotes reaction time and catalyst turnover in asymmetric Suzuki-Miyaura cross-coupling reactions was conducted in this research. The novel hexaarylbenzene-based phosphonite ligands which have chiral BINOL moieties were successfully synthesized : one of them has achieved to cross-couple 2-chlro-3-methoxybenzaldehyde with ortho-tolylboronic acid in TON 750 for 4 h, giving 75% and 76% ee. On the other hand, the elaboration was found in the reactions of sterically hindered substrates and the further development of phosphonite ligands.

Research Products

• [Journal Article] Asymmetric Suzuki-Miyaura cross-coupling reaction of aryl chlorides with enhancement of reaction time and catalyst turnover (2011)
  • Author(s): Akihiro H. Sato, Maeda Mine, Mihara Shigenori, Iwasawa, Tetsuo
  • Journal Title: Tetrahedron Letters Volume: 52巻、21号 Pages: 2638-2641
  • Peer Reviewed
• [Journal Article] Asymmetric Suzuki-Miyaura cross-coupling reaction of aryl chlorides with enhancement of reaction time and catalyst turnover (2011)
  • Author(s): 亀井俊徳、佐藤明広、岩澤哲郎
  • Journal Title: Tetrahedron Letters Volume: 52(印刷中)
  • Peer Reviewed
• [Presentation] Asymmetric Suzuki-Miyaura cross-coupling of aryl chlorides with enhancement of raction time and catalyst turnover (2011)
  • Author(s): 佐藤明広、岩澤哲郎
  • Organizer: 日本プロセス化学会
  • Place of Presentation: 京都府京都市(京都国際会議場)
  • Year and Date: 2011-08-12
• [Presentation] Asymmetric Suzuki-Miyaura cross-coupling of aryl chlorides with enhancement of raction time and catalyst turnover (2011)
  • Author(s): 佐藤明広、岩澤哲郎
  • Organizer: The 2nd International Symposium on Process Chemistry
  • Place of Presentation: Kyoto International Conference Center (Kyoto, Japan)
  • Year and Date: 2011-08-12
• [Patent(Industrial Property Rights)] 不斉ホスホナイト化合物、不斉合成触媒、不斉ホスホナイト化合物の製造方法、光学活性を有する有機化合物の製造方法 (2011)
  • Inventor(s): 岩澤哲郎、佐藤明広
  • Industrial Property Rights Holder: 岩澤哲郎、佐藤明広、学校法人龍谷大学
  • Industrial Property Number: 2011-003507
  • Filing Date: 2011-01-11
• [Patent(Industrial Property Rights)] 不斉ホスホナイト化合物、不斉合成触媒、不斉ホスホナイト化合物の製造方法、光学活性を有する有機化合物の製造方法 (2011)
  • Inventor(s): 佐藤明広、岩澤哲郎
  • Industrial Property Rights Holder: 佐藤明広、岩澤哲郎、龍谷大学
  • Industrial Property Number: 2011-003507
  • Filing Date: 2011-01-11