Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes

Pawan K Dhondi; John D Chisholm

doi:10.1021/ol0525260

Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes

Org Lett. 2006 Jan 5;8(1):67-9. doi: 10.1021/ol0525260.

Authors

Pawan K Dhondi¹, John D Chisholm

Affiliation

¹ Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, New York 13244, USA.

PMID: 16381569
DOI: 10.1021/ol0525260

Abstract

[reaction: see text] The rhodium-catalyzed addition of alkynes to 1,2-diketones, 1,2-ketoesters, and aldehydes provides a method for the synthesis of tertiary alkynyl alcohols under mild conditions. The reaction tolerates many functional groups (such as carboxylic acids) that are incompatible with other methods. The alkyne addition reaction proceeds best using bulky phosphine ligands such as 2-(di-tert-butylphosphino)biphenyl. This method fills a void in the more common zinc-catalyzed processes, which give poor yields with enolizable 1,2-dicarbonyl substrates.