Dearomative Difunctionalization Spirocyclization of Unactivated Arenes without a Catalyst

Abstract

Herein, we present an intermolecular dearomative spirocyclization/1,4-alkyl oximation of unactivated arenes. This catalyst-free strategy relies on the photochemical N–N bond cleavage of N-nitrosamines to produce nitrogen-centered radicals. By integrating an amidyl radical transfer strategy with DABSO-mediated trapping of the nitrogen-centered radicals, this method enables the simultaneous difunctionalization of alkenes and formal dearomative spirocyclization of unactivated arenes.