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Visible-Light-Induced Cascade Arylazidation of Activated Alkenes with Trimethylsilyl Azide
Xinzhuang Wu1, Xinyi Zhang1, Xiaochen Ji1,2
1Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
Abstract:
A visible-light-induced cascade arylazidation of activated alkenes with trimethylsilyl azide (TMSN3) has been developed. Mechanistic investigations reveal that the single electron transfer (SET) of TMSN3 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.
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