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Synthesis of α,α‐Difluoromethylene Alkynes by Palladium‐Catalyzed gem ‐Difluoropropargylation of Aryl and Alkenyl Boron Reagents
Author(s) -
Yu YanBo,
He GuoZhen,
Zhang Xingang
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405204
Subject(s) - palladium , chemistry , reagent , regioselectivity , aryl , catalysis , combinatorial chemistry , boron , organic synthesis , functional group , coupling reaction , molecule , organic chemistry , alkyl , polymer
gem ‐Difluoropropargyl bromides are versatile intermediates in organic synthesis, but have rarely been employed in transition‐metal‐catalyzed cross‐coupling reactions. The first palladium‐catalyzed gem ‐difluoropropargylation of organoboron reagents with gem ‐difluoropropargyl bromides is now reported. The reaction proceeds under mild reaction conditions with high regioselectivity; it features a broad substrate scope and excellent functional‐group compatibility and thus provides an attractive approach for the synthesis of complex fluorinated molecules, in particular for drug discovery and development.

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