Issue 18, 2023

Photoinduced regioselective difluorination of secondary inert C(sp3)–H bonds in sulfonamides via 1,5-hydrogen-atom transfer

Abstract

Difluorinated compounds are important structural motifs in organic synthesis and medicinal chemistry because fluoride can modulate the properties of various molecules. In this paper, we present an efficient and convenient method for achieving difluorination of inert C(sp3)–H bonds based on an N-directed 1,5-hydrogen-atom transfer (1,5-HAT) strategy. This difluorination approach tolerates various functional groups and allows for the late-stage difluorination of complex molecules. The proposed mechanism involves the formation of an amine radical cation and a radical chain propagation process, which also provides a new avenue of nitrogen-centered radical generation for the 1,5-HAT reaction.

Graphical abstract: Photoinduced regioselective difluorination of secondary inert C(sp3)–H bonds in sulfonamides via 1,5-hydrogen-atom transfer

Supplementary files

Article information

Article type
Research Article
Submitted
20 Jun 2023
Accepted
05 Aug 2023
First published
09 Aug 2023

Org. Chem. Front., 2023,10, 4709-4717

Photoinduced regioselective difluorination of secondary inert C(sp3)–H bonds in sulfonamides via 1,5-hydrogen-atom transfer

Z. Chen, W. Zhu, C. Wang, N. Xu, Q. Jin, X. Huang, S. Song and J. Li, Org. Chem. Front., 2023, 10, 4709 DOI: 10.1039/D3QO00931A

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