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

Guangzhu Wang; Chaoren Shen; Xinyi Ren; Kaiwu Dong

doi:10.1039/d1cc04996h

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

Chem Commun (Camb). 2022 Jan 25;58(8):1135-1138. doi: 10.1039/d1cc04996h.

Authors

Guangzhu Wang¹, Chaoren Shen¹, Xinyi Ren¹, Kaiwu Dong¹

Affiliation

¹ Chang-Kung Chuang Institute, and Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, P. R. China. kwdong@chem.ecnu.edu.cn.

PMID: 34981092
DOI: 10.1039/d1cc04996h

Abstract

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.