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

Yanmei Lin; Xiaomin Shu; Haohua Huo

doi:10.1055/s-0043-1763660

Synthesis, Table of Contents

Synthesis 2024; 56(11): 1702-1710
DOI: 10.1055/s-0043-1763660

paper

New Trends in Organic Synthesis from Chinese Chemists

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

Yanmei Lin

,

Xiaomin Shu

,

Haohua Huo ∗

Abstract

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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

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References

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