Copper-catalyzed double N-alkenylation of amides: an efficient synthesis of di- or trisubstituted N-acylpyrroles

Xiyuan Yuan; Xiaobing Xu; Xiaobo Zhou; Jiwei Yuan; Lugen Mai; Yanzhong Li

doi:10.1021/jo062194s

Copper-catalyzed double N-alkenylation of amides: an efficient synthesis of di- or trisubstituted N-acylpyrroles

J Org Chem. 2007 Feb 16;72(4):1510-3. doi: 10.1021/jo062194s. Epub 2007 Jan 24.

Authors

Xiyuan Yuan¹, Xiaobing Xu, Xiaobo Zhou, Jiwei Yuan, Lugen Mai, Yanzhong Li

Affiliation

¹ Department of Chemistry and Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China.

PMID: 17249731
DOI: 10.1021/jo062194s

Abstract

An efficient copper-catalyzed double alkenylation of amides with (1Z,3Z)-1,4-diiodo-1,3-dienes is reported for the first time. The reactions proceed to afford di- or trisubstituted N-acylpyrroles in good to excellent yields using CuI as the catalyst, Cs2CO3 as the base, and rac-trans-N,N'-dimethylcyclohexane-1,2-diamine as the ligand.

Publication types

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