Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides

Yanshi Zhang; Richard P Hsung; Michael R Tracey; Kimberly C M Kurtz; Eymi L Vera

doi:10.1021/ol049827e

Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides

Org Lett. 2004 Apr 1;6(7):1151-4. doi: 10.1021/ol049827e.

Authors

Yanshi Zhang¹, Richard P Hsung, Michael R Tracey, Kimberly C M Kurtz, Eymi L Vera

Affiliation

¹ Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.

PMID: 15040745
DOI: 10.1021/ol049827e

Abstract

A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO(4).5H(2)O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.