Ni-Catalyzed enantioselective reductive arylcyanation/cyclization of N-(2-iodo-aryl) acrylamide

A Ni/(S,S)-BDPP-catalyzed intramolecular Heck cyclization of N-(2-iodo-aryl) acrylamide with 2-methyl-2-phenylmalononitrile was developed to give oxindoles with good enantioselectivities. We found that utilizing such an electrophilic cyanation reagent could tackle the deleterious effect of the coordinative cyanide ion in the asymmetric alkene arylcyanation.

Automated summary

An intramolecular Heck cyclization catalyzed by Ni/(S,S)-BDPP was developed for the synthesis of oxindoles with good enantioselectivities. The use of an electrophilic cyanation reagent was found to address the deleterious effect of the coordinative cyanide ion in asymmetric alkene arylcyanation.