Strain-release driven α,β-difunctionalization of cyclopropanols with bromonaphthols†

Abstract

Naphthofuran skeletons serve as pivotal structural constituents in plenty of bioactive molecules and luminescent materials. Herein, we present an unprecedented Zn-catalyzed aerobic oxidative ring-opening/[3 + 2] cyclization cascade of cyclopropanols with bromonaphthols, providing an eco-friendly and modular approach for synthesizing naphthofuran derivatives with diverse functional groups. Mechanistic studies revealed that the reaction proceeds through the ring-opening of cyclopropanols, a Michael addition, and an interrupted S_NR1/radical coupling pathway.