Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents

Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale throug...

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Bibliographic Details
Published in:Organic letters 2023-08, Vol.25 (33), p.6200-6205
Main Authors: Yedase, Girish Suresh, Arif, Munaifa, Kuniyil, Rositha, Yatham, Veera Reddy
Format: Article
Language:English
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Summary:Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale through simply cyclocondensation of commercially available anthranilamide with phenyltrifluoro or difluoromethyl ketone. Preliminary mechanistic studies indicated that a canonical photoredox catalytic cycle is being operative. DFT studies support this and further reveal that deprotonation occurs before radical cleavage. DFT studies also show that the better yield with HCF2 reagent is attributed to the favorable expulsion of the corresponding radical moiety.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02413