Tribromide enabled step-up generation of spirolactams from esters employing oxidative dearomatization of arenols

Abstract

Synthetically challenging spirolactams were developed in good yields and regio-selectivity through a step-up oxidative dearomatization of easily accessible arenols tethered to esters in the presence of quaternary ammonium tribromide as an economic oxidant and amines. The reaction mechanism associated with this unprecedented dearomative lactamisation has been forecasted with a series of controlled experiments and DFT studies. © 2024 The Royal Society of Chemistry.