Stereoselective Copper-Catalyzed Cross-Coupling of Aziridines with Benzimidazoles via Nucleophilic Ring Opening and C(sp2)-H Functionalization

Pinaki Bhusan De; Sourav Pradhan; Tharmalingam Punniyamurthy

doi:10.1021/acs.joc.7b00265

Stereoselective Copper-Catalyzed Cross-Coupling of Aziridines with Benzimidazoles via Nucleophilic Ring Opening and C(sp²)-H Functionalization

J Org Chem. 2017 Mar 17;82(6):3183-3191. doi: 10.1021/acs.joc.7b00265. Epub 2017 Mar 6.

Authors

Pinaki Bhusan De¹, Sourav Pradhan¹, Tharmalingam Punniyamurthy¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781039, India.

PMID: 28234479
DOI: 10.1021/acs.joc.7b00265

Abstract

A copper-catalyzed cross-coupling of 2-alkyl-/2-arylaziridines with benzimidazoles is reported. The reactions involve a regiospecific ring opening of aziridines with benzimidazoles to give benzoimidazolylethylamine derivatives that lead to dehydrogenative cross-coupling between C(sp²)-H and N-H bonds to produce dihydroimidazobenzimidazoles. Optically active 2-arylaziridines can be stereoinvertivebly cross-coupled with high enantiomeric purities (77-97% ee). These aerobic catalytic systems comprise an inexpensive Cu(II) salt and PCy₃ ligand at moderate temperature.

Publication types

Research Support, Non-U.S. Gov't