Visible Light-Mediated Dearomative Remote Functionalization of Arenes via a Tandem Strain-Release Spirocyclization Relay.

Abstract

Tandem strain-release addition cyclization reactions in bicyclo[1.1.0]butanes (BCBs) present a versatile platform for rapidly creating molecular complexity. While lactams and indolinones have been accessed using alkenes and arenes as appendages via this strategy, the dearomative functionalization of arenes remains unexplored. This work demonstrates a photocatalyst-free, visible light-mediated blueprint for the remote functionalization of arenes in tandem with a strain-release framework. Nitrosamines are utilized as versatile reagents for installing sulfonamides and oximes, leading to intricately designed 3D spirocyclic structures bearing medicinally relevant functionalities.