Synthesis of Succinimide Spiro-Fused Sultams from the Reaction of N-(Phenylsulfonyl)acetamides with Maleimides via C(sp2)-H Activation.

Abstract

Presented herein is an effective preparation of succinimide spiro-fused sultams through the coupling reaction of N-(phenylsulfonyl)acetamides with maleimides. It is deduced that this reaction should proceed through a cascade process including Rh(III)-catalyzed C(sp2)-H bond cleavage of N-(phenylsulfonyl)acetamide, maleimide double bond insertion into the C-Rh bond, β-hydride elimination, reductive elimination, and intramolecular aza-Michael addition. Notably, this cascade procedure features simultaneous annulation and spirocyclization through traceless fusion of the directing group into target product by using air as an economical oxidant to assist the regeneration of the active Rh(III) catalyst. This new method has several advantages including readily accessible starting materials with broad scope, significantly reduced synthetic steps, redox-neutral conditions, high atom-economy, and sustainability.