Selective C(sp2)-C(sp) bond cleavage: the nitrogenation of alkynes to amides

Chong Qin; Peng Feng; Yang Ou; Tao Shen; Teng Wang; Ning Jiao

doi:10.1002/anie.201303376

Selective C(sp2)-C(sp) bond cleavage: the nitrogenation of alkynes to amides

Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7850-4. doi: 10.1002/anie.201303376. Epub 2013 Jun 26.

Authors

Chong Qin¹, Peng Feng, Yang Ou, Tao Shen, Teng Wang, Ning Jiao

Affiliation

¹ State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing 100191, China.

PMID: 23804537
DOI: 10.1002/anie.201303376

Abstract

Breakthrough: A novel catalyzed direct highly selective C(sp2)-C(sp) bond functionalization of alkynes to amides has been developed. Nitrogenation is achieved by the highly selective C(sp2)-C(sp) bond cleavage of aryl-substituted alkynes. The oxidant-free and mild conditions and wide substrate scope make this method very practical.

Keywords: CC bond cleavage; alkynes; amides; gold; rearrangement.

Publication types

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

MeSH terms

Alkynes / chemistry*
Amides / chemistry*
Catalysis
Cyclization
Molecular Structure
Nitrogen / chemistry*
Oxidants / chemistry
Oxidation-Reduction
Stereoisomerism

Substances

Alkynes
Amides
Oxidants
Nitrogen