Organic Chemistry Portal

Abstracts

Search:

Copper-Catalyzed Cross-Coupling of Vinylsiloxanes with Bromoalkynes: Synthesis of Enynes

Lo´c Cornelissen, Maxime Lefrancq and Olivier Riant*

*UniversitÚ Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium, Email: Olivier.riantuclouvain.be

L. Cornelissen, M. Lefrancq, O. Riant, Org. Lett., 2014, 16, 3024-3027.

DOI: 10.1021/ol501140p (free Supporting Information)


see article for more reactions

Abstract

A mild and efficient copper-catalyzed Hiyama-type cross-coupling of vinylsiloxanes with bromoalkynes enables the formation of various sensitive enynes. Cis, trans, and 1,1′-disubstituted vinylsiloxanes can be converted with full retention of stereochemistry. Sensitive groups such as halides, unsaturated ketones, and aldehydes are fully tolerated.

see article for more examples



Key Words

enynes


ID: J54-Y2014