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Expedient Trifluoromethylacylation of Styrenes Enabled by Photoredox Catalysis

Lu Wang, Heng Zhang, Chuan Zhu, Chao Feng

2021Chinese Journal of Chemistry20 citationsDOI

Abstract

Comprehensive Summary Herein, we disclosed a photoredox enabled protocol for trifluoromethylacylation of styrenes through a radical‐carboanion cascade and subsequent oxidation. With a broad range of aldehydes and inexpensive Langlois reagent as acyl and CF 3 precursor, respectively, the alkene motif could be readily converted into β‐trifluoromethyl ketones in moderate to good yields and with excellent regioselectivity. Besides CF 3 , di‐, mono‐ and non‐fluorinated C‐radicals were revealed amenable in this reaction, providing good opportunity for the construction of structurally diverse ketones of interest in pharmaceutical research. Additionally, the utility of this protocol was further demonstrated by successful extension to trifluoromethylarylation and ‐alkylation by employing arylcyanide or acrylates in place of carbonyls.

Topics & Concepts

ChemistryRegioselectivityAlkeneReagentRadicalAlkylationCombinatorial chemistryPhotoredox catalysisTrifluoromethylOrganic chemistryCatalysisPhotocatalysisAlkylFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
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