A visible light-promoted generation of nitrilium ions from diazoacetates and nitriles has been developed. The reaction utilized visible light transformation of diazoacetates to the free carbene that could be trapped by nitriles to generate nitrilium ions, followed by nucleophilic attack on the benzotriazoles and carboxylic acids. This protocol provides an efficient and practical approach to N-imidoylbenzotriazoles and diacylglycine esters in good to excellent yields.

A visible-light photocatalytic regioselective difunctionalization of alkenes with diazo compounds and tert-butyl nitrite has been developed. The protocol provides an efficient approach to γ-oximino esters under mild conditions. Significantly, this transformation not only shows the good compatibility of nucleophilic diazo compounds and electrophilic tert-butyl nitrite but also displays diazo compounds generating alkyl radicals that preferred addition to alkenes over nitroso radicals.

A visible light-induced carbene reactivity of acceptor diazoalkanes has been developed toward synthesis of difunctionalized ethers from cyclic ethers and various N/O/S nucleophiles. The carbene transfer reactions involve oxonium ylide...

Here, we report a mild and highly efficient approach to alkyl oxazoles through merging gold/copper catalysis and copper/photoredox catalysis. Various alkyl oxazoles are synthesized from N-propargylamides with alkyl halides in good to excellent yields with wide functional-group compatibility under blue-light irradiation. Significantly, a copper catalyst plays a dual role in this transformation: as a powerful cocatalyst to accelerate protodeauration of vinyl gold intermediates and improve photoredox catalysis.