Copper-mediated oxidative decarboxylative coupling of arylpropiolic acids with dialkyl H-phosphonates in water

Xiang Li; Fan Yang; Yangjie Wu; Yusheng Wu

doi:10.1021/ol4037242

Copper-mediated oxidative decarboxylative coupling of arylpropiolic acids with dialkyl H-phosphonates in water

Org Lett. 2014 Feb 7;16(3):992-5. doi: 10.1021/ol4037242. Epub 2014 Jan 29.

Authors

Xiang Li¹, Fan Yang, Yangjie Wu, Yusheng Wu

Affiliation

¹ The College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University , Zhengzhou 450052, People's Republic of China.

PMID: 24476094
DOI: 10.1021/ol4037242

Abstract

An efficient, mild, and generally applicable protocol for copper-mediated oxidative decarboxylative coupling of arylpropiolic acids with dialkyl H-phosphonates in water has been developed. Note that the reaction could proceed smoothly under air at relatively low temperature (60 °C), and the addition of isopropanol could successfully suppress the decomposition of dialkyl H-phosphonates in water.

Publication types

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

MeSH terms

Alkynes / chemical synthesis*
Alkynes / chemistry*
Catalysis
Copper / chemistry*
Molecular Structure
Organophosphonates / chemical synthesis*
Organophosphonates / chemistry*
Oxidative Coupling
Propionates / chemical synthesis*
Propionates / chemistry*
Water / chemistry*

Substances

Alkynes
Organophosphonates
Propionates
Water
Copper
propiolic acid