Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 5, Pages 1863-1870Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912450
Keywords
fluoroketone; multicomponent reaction; N-heterocyclic carbene organocatalysis; olefin difunctionalization; radical acylfluoroalkylation
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Funding
- NSFC [21871031, 21702021, 81573588, 81703809]
- Science & Technology Department of Sichuan Province [2017JQ0032]
- Thousand Talents Program of Sichuan Province
- Chengdu Talents Program
- Chengdu University
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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.
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