Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: facile synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols

Ting Li; Zhen Wang; Mingliang Zhang; Hui-Jun Zhang; Ting-Bin Wen

doi:10.1039/c5cc01412c

Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: facile synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols

Chem Commun (Camb). 2015 Apr 21;51(31):6777-80. doi: 10.1039/c5cc01412c.

Authors

Ting Li¹, Zhen Wang, Mingliang Zhang, Hui-Jun Zhang, Ting-Bin Wen

Affiliation

¹ Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, Fujian, P. R. China. chwtb@xmu.edu.cn.

PMID: 25786197
DOI: 10.1039/c5cc01412c

Abstract

An unusual Rh/Cu-catalyzed synthesis of pyrido[2,1-a]indoles starting from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols was presented. The multi-step cascade transformations formally involve the cleavage of two C-H, three C-C, and one C-N bonds with concomitant construction of two C-H, four C-C, and one C-N bonds with excellent chemoselectivity in one-pot reaction.