Ni-Catalyzed Reductive Arylcyanation of Alkenes

We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyanosubstituted oxindoles and isoquinoline-1,3-diones and features high functional group tolerance. In addition, an enantioselective version was developed for the construction of enantiomerically enriched 3-cyanomethyl oxindole. This method has also been applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.

Automated summary

A Ni-catalyzed reductive arylcyanation of alkene using an environmentally benign and nontoxic organo cyanating reagent has been developed. This method allows for the rapid synthesis of cyanosubstituted oxindoles and isoquinoline-1,3-diones with high functional group tolerance, and also features an enantioselective version for the construction of enantiomerically enriched 3-cyanomethyl oxindoles. Additionally, this approach has been successfully applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.