open access

https://hdl.handle.net/2115/80568

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

英語

2020-02-04

American Chemical Society

Journal of organic chemistry

85(6)

4172-4181

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.

学術雑誌論文

Accepted Manuscript

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.joc.9b03353.

0022-3263