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Nitrogen central radicals (NCRs) are versatile synthetic intermediates for creating functional nitrogen-containing molecules. Herein, a photosensitized β-sulfonylamination of terminal alkynes as well as acetylene has been established by employing N-sulfonyl heteroaromatics as bifunctional reagents (BFRs) to efficiently deliver versatile (E)-β-sulfonylvinylamines with excellent regio- and stereoselectivities. Mechanistic studies suggest a base-accelerated energy transfer (EnT) photocatalysis involving aromatic NCR formation, radical addition to alkynes, and sulfonylation processes.

Visible-light-promoted thiolation of benzyl chlorides with thiosulfonates is disclosed via an electron donor–acceptor complex strategy. In addition to efficiently delivering a series of arylbenzylsulfide compounds, versatile thioglycosides were also successfully constructed by applying the metal- and photocatalyst-free protocol. Preliminary mechanistic studies suggest that a radical–radical coupling process was involved in this transformation.