Abstract
Various sulfone tetrazoles were activated via iridium photoredox catalysis in the presence of DMAP to give dialkyl sulfones. The presumed sulfone radical intermediates were trapped by a range of electron-deficient olefins in generally good to excellent yields.
Highlights
C ompared to carbon−carbon bond formation using photocatalytic methods,[1] carbon−sulfur coupling processes are less well-known[2] but are growing in popularity owing to their presence in pharmaceutical and agrochemical agents.[3]
Sulfone-substituted tetrazoles have been featured most notably as partners in the Julia/Kocienski olefination process,[10] while recently they were used in nickelcatalyzed cross-coupling with organozinc reagents via reductive desulfonylation through a single-electron transfer mechanism.[11]
In a preliminary experiment we found the sulfone moiety is retained in the product where sulfone-substituted Nphenyl tetrazole (1a) was subjected to an iridium catalyst system with blue LED irradiation using ethyl acrylate (2a) as a radical trap to give compound 3a in modest yield (Scheme 1).[12]
Summary
We have demonstrated that sulfone-substituted N-phenyltetrazoles undergo efficient photoredox coupling with acrylates and related electron-withdrawing olefinic acceptors to DSC data commentary. We give coupled products retaining the sulfone moiety, suggesting thank the American Chemical Society through the Arthur C. the intermediacy of sulfonyl radicals. Reaction yields are Cope Fund (award to S.V.L.). The authors gratefully generally very good and occur with high substrate tolerance of functionality. The products of these reactions could find useful applications in medicinal chemistry programs[19] or as precursors in further Ramberg−Backlund reactions, for example.
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