Rhodium-catalyzed tandem acylmethylation/annulation of N-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazole N-oxides

Abstract

An atom-economical protocol for synthesizing indazole N-oxides from readily available N-nitrosoanilines and sulfoxonium ylides through the rhodium(III)-catalyzed C–H activation and cyclization reaction is described here. This protocol employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate to good yields under an ambient atmosphere, providing a straightforward approach to access structurally diverse and valuable indazole N-oxide derivatives. Importantly, this new annulation process represents a hitherto unobserved reactivity pattern for the N-nitroso group.