Radical photochemical difluorosulfoximination of alkenes and propellanes
Simone Baldon1, Julien Paut1,2, Elsa Anselmi2,3
1Department of Chemical Sciences, University of Padova Via Francesco Marzolo 1 35131 Padova Italy sara.cuadroshuertas@unipd.it luca.dellamico@unipd.it.
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.
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