Issue 16, 2025

Radical photochemical difluorosulfoximination of alkenes and propellanes

Abstract

Herein, we report a metal-free divergent visible-light driven method for the synthesis of fluorinated sulfoximines. Both olefins and propellanes efficiently undergo difluorosulfoximination with yields up to 77% (65 examples). The process is general and robust and tolerates diverse functional groups, including esters, ethers, ketones, silyl groups, silyl ethers or boronic esters. The functionalization of diverse bioactive ingredients (8 examples) and various product manipulations demonstrate the synthetic usefulness of the developed synthetic platform. Finally, we rationalized the divergent reaction mechanism by performing Stern–Volmer quenching and EPR experiments that revealed the key activity of a difluoroalkyl sulfoximine radical.

Graphical abstract: Radical photochemical difluorosulfoximination of alkenes and propellanes

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Article information

Article type
Edge Article
Submitted
11 Feb 2025
Accepted
12 Mar 2025
First published
14 Mar 2025
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2025,16, 6957-6964

Radical photochemical difluorosulfoximination of alkenes and propellanes

S. Baldon, J. Paut, E. Anselmi, G. Dagousset, B. Tuccio, G. Pelosi, S. Cuadros, E. Magnier and L. Dell’Amico, Chem. Sci., 2025, 16, 6957 DOI: 10.1039/D5SC01068C

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