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

A visible-light-induced cascade arylazidationof activated alkeneswith trimethylsilyl azide (TMSN3) has been developed. Mechanisticinvestigations reveal that the single electron transfer (SET) of TMSN3 with the excited photocatalyst was involved in the initialstep, followed by radical addition/aryl migration/desulfonylationto furnish valuable & alpha;-aryl-& beta;-azido amides and azidatedoxindoles under mild conditions, which are versatile building blocksin organic synthesis. With simple treatment, the obtained arylazidatedproducts were further converted to valuable & beta;-amino amide and1,2,3-triazole derivatives.

Automated summary

A cascade arylazidation reaction of activated alkenes with trimethylsilyl azide (TMSN3) under visible-light irradiation has been developed. Mechanistic investigations reveal that the reaction proceeds via single electron transfer (SET) between TMSN3 and the excited photocatalyst, followed by radical addition/aryl migration/desulfonylation to yield valuable α-aryl-β-azido amides and azidated oxindoles as versatile building blocks in organic synthesis. The obtained arylazidated products can be further converted to valuable β-amino amide and 1,2,3-triazole derivatives with simple treatment.