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Pd‐Catalyzed Regioselective Activation of gem ‐Difluorinated Cyclopropanes: A Highly Efficient Approach to 2‐Fluorinated Allylic Scaffolds
Author(s) -
Xu Jun,
Ahmed EbrahimAlkhalil,
Xiao Bin,
Lu QianQian,
Wang YunLong,
Yu ChuGuo,
Fu Yao
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502308
Subject(s) - regioselectivity , chemistry , catalysis , allylic rearrangement , combinatorial chemistry , alkylation , bond cleavage , tsuji–trost reaction , selectivity , molecule , cleavage (geology) , stereochemistry , organic chemistry , materials science , fracture (geology) , composite material
Abstract An unprecedented Pd‐catalyzed regioselective activation of gem‐difluorinated cyclopropanes induced by CC bond cleavage is reported. It provides a general and efficient access to a variety of 2‐fluoroallylic amines, ethers, esters, and alkylation products in high Z‐selectivity, which are important skeletons in many biologically active molecules. In addition, the transformation represents the first general application of gem‐difluorinated cyclopropanes as reaction partners in transition‐metal‐catalyzed cross‐coupling reaction.