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Radical Acylfluoroalkylation of Olefins through N‐Heterocyclic Carbene Organocatalysis
Author(s) -
Li JunLong,
Liu YanQing,
Zou WenLin,
Zeng Rong,
Zhang Xiang,
Liu Yue,
Han Bo,
He Yu,
Leng HaiJun,
Li QingZhu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201912450
Subject(s) - carbene , organocatalysis , stereocenter , regioselectivity , chemistry , olefin fiber , combinatorial chemistry , catalysis , organic chemistry , yield (engineering) , enantioselective synthesis , materials science , metallurgy
Fluorinated ketones are widely prevalent in numerous biologically interesting molecules, and the development of novel transformations to access these structures is an important task in organic synthesis. Herein, we report the multicomponent radical acylfluoroalkylation of a variety of olefins in the presence of various commercially available aromatic aldehydes and fluoroalkyl reagents through N‐heterocyclic carbene organocatalysis. With this protocol, over 120 examples of functionalized ketones with diverse fluorine substituents have been synthesized in up to 99 % yield with complete regioselectivity. The generality of this catalytic strategy was further highlighted by its successful application in the late‐stage functionalization of pharmaceutical skeletons. Excellent diastereoselectivity could be achieved in the reactions forging multiple stereocenters. In addition, preliminary results have been achieved on the catalytic asymmetric variant of the olefin difunctionalization process.