Palladium(II)-catalyzed sequential C-H arylation/aerobic oxidative C-H amination: one-pot synthesis of benzimidazole-fused phenanthridines from 2-arylbenzimidazoles and aryl halides

Gongyuan Zhao; Chunxia Chen; Yixia Yue; Yanhan Yu; Jinsong Peng

doi:10.1021/jo502632b

Palladium(II)-catalyzed sequential C-H arylation/aerobic oxidative C-H amination: one-pot synthesis of benzimidazole-fused phenanthridines from 2-arylbenzimidazoles and aryl halides

J Org Chem. 2015 Mar 6;80(5):2827-34. doi: 10.1021/jo502632b. Epub 2015 Feb 13.

Authors

Gongyuan Zhao¹, Chunxia Chen, Yixia Yue, Yanhan Yu, Jinsong Peng

Affiliation

¹ Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University , NO. 26 Hexing Road, Harbin 150040, P. R. China.

PMID: 25658883
DOI: 10.1021/jo502632b

Abstract

Starting from 2-arylbenzimidazoles and aryl halides, an efficient palladium-based catalytic method for the synthesis of benzimidazole-fused phenanthridines has been developed. This reaction sequence comprises intermolecular C-H arylation and intramolecular aerobic oxidative C-H amination, involving the rupture of two C-H bonds, one C-X bond, and one N-H bond in one pot. The Pd(II)-Pd(IV)-Pd(II) and Pd(II)-Pd(0)-Pd(II) catalytic cycles work together under the reported conditions to generate phenanthridines with diverse substituents.