Photoredox-Catalyzed C(sp³)–H Difluoroallylation of Amides

Abstract

A photoredox-catalyzed, bromine-radical-mediated C(sp³)–H difluoroallylation of amides is disclosed. This modular approach exploits the hydrogen atom transfer (HAT) ability of photooxidatively generated bromine radicals to convert both cyclic and acyclic amides into the corresponding α-amino alkyl radicals that then are coupled with readily available trifluoromethyl alkenes. This method is distinguished by its mild conditions, broad substrate scope (30 examples), and the use of a simple HAT reagent, namely sodium bromide (NaBr). This strategy offers a promising paradigm for the incorporation of carbonyl isosteres into saturated aliphatic amines.

Key words

photoredox catalysis - HAT - difluoroallylation - amides - bromine radical

Publication History

Received: 10 October 2023

Accepted after revision: 27 November 2023

Article published online:
03 January 2024

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