Visible-Light-Induced Cascade Arylazidation of Activated Alkenes with Trimethylsilyl Azide.

A visible-light-induced cascade arylazidation of activated alkenes with trimethylsilyl azide (TMSN 3 ) has been developed. Mechanistic investigations reveal that the single electron transfer (SET) of TMSN 3 with the excited photocatalyst was involved in the initial step, followed by radical addition/aryl migration/desulfonylation to furnish valuable α-aryl-β-azido amides and azidated oxindoles under mild conditions, which are versatile building blocks in organic synthesis. With simple treatment, the obtained arylazidated products were further converted to valuable β-amino amide and 1,2,3-triazole derivatives.