Copper(I)-Catalyzed Boryl Substitution of 1-Trifluoromethyl Allenes for the Synthesis of 3-Boryl-Substituted 1,1-<i>gem</i>-Difluorodienes

• Akiyama, Sota

• Nomura, Syogo

• Kubota, Koji

• Ito, Hajime

書誌事項

タイトル別名

• Copper(I)-Catalyzed Boryl Substitution of 1-Trifluoromethyl Allenes for the Synthesis of 3-Boryl-Substituted 1,1-gem-Difluorodienes

抄録

A method to synthesize 3-boryl-1,1-gem-difluorodienes via the copper(I)-catalyzed boryl substitution of trifluoromethyl-substituted allenes was developed. The borylated compounds were obtained up to 91% yield with excellent selectivity. We proposed that the reaction proceeded via gamma-selective borylcupration into the trifluoromethyl-substituted alien; followed by copper(I)-beta-fluoro elimination. Subsequent transformations of the borylation product by Suzuki-Miyaura cross-coupling or Diels-Alder reaction provided various compounds bearing a difluoro moiety, which are difficult to synthesize by existing methods.

収録刊行物

• Journal of organic chemistry

  Journal of organic chemistry 85 (6), 4172-4181, 2020-02-04

  American Chemical Society

キーワード

• Organic Chemistry

詳細情報

• CRID: 1050850313390910336
• NII論文ID: 120006978440
• DOI: 10.1021/acs.joc.9b03353
• ISSN: 15206904
• ISSN: 00223263
• HANDLE: 2115/80568
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.joc.9b03353
• 本文言語コード: en
• 資料種別: journal article
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