Copper-Catalyzed Radical Aryl Migration Approach for the Preparation of Cyanoalkylsulfonylated Oxindoles/Cyanoalkyl Amides

A copper-catalyzed radical cross-coupling of oxime esters and activated alkenes is accomplished for the synthesis of cyanoalkylsulfonylated oxindoles and cyanoalkyl amides via an aryl migration strategy. Specifically, the subsequent mechanism research indicates that the unique desulfonylation and sulfone addition processes were involved in the transformation. This transformation is identified as having good functional group applicability with two different quaternary stereocenter in a regioselective manner, which is controlled by the substituent group of the nitrogen.

Automated summary

The copper-catalyzed radical cross-coupling of oxime esters and activated alkenes successfully produced cyanoalkylsulfonylated oxindoles and cyanoalkyl amides through an aryl migration strategy, with unique desulfonylation and sulfone addition processes involved. The transformation demonstrates good functional group applicability, enabling the regioselective control of two different quaternary stereocenters by the substituent group of the nitrogen atom.