Organic Chemistry Portal



Copper-Catalyzed Synthesis of 2,4-Disubstituted Allenoates from α-Diazoesters

Matthew Hassink, Xiaozhong Liu and Joseph M. Fox*

*Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email:

M. Hassink, X. Liu, J. M. Fox, Org. Lett., 2011, 13, 2388-2391.

DOI: 10.1021/ol2006242

see article for more reactions


A Cu-catalyzed coupling of α-substituted-α-diazoesters with terminal alkynes gives substituted allenoates. Key to the development of a selective method was the recognition that an adventitous base catalyzes the isomerization to form the allenoate product. A plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.

see article for more examples

Key Words


ID: J54-Y2011-1370