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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:

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

DOI: 10.1021/ol501140p (free Supporting Information)

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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.

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Key Words


ID: J54-Y2014