Copper-catalyzed cross-coupling of vinylsiloxanes with bromoalkynes: Synthesis of enynes

Cornelissen, Loïc;Lefrancq, Maxime;Riant, Olivier
(2014) Organic Letters — Vol. 16, n° 11, p. 3024-3027 (2014)

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  • Cornelissen, LoïcUCLouvain
    Author
  • Lefrancq, MaximeUCLouvain
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  • Author
Abstract
Enynes are versatile building blocks in organic synthesis. A copper-catalyzed Hiyama-type cross-coupling of vinylsiloxanes with bromoalkynes is presented. This mild and efficient method led to the formation of various sensitive enynes. The use of cis, trans, and 1,1′-disubstituted vinylsiloxanes was allowed, and full retention of stereochemistry was observed. Sensitive groups such as halides, unsaturated ketones, and aldehydes were fully tolerated. © 2014 American Chemical Society.
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Cornelissen, L., Lefrancq, M., & Riant, O. (2014). Copper-catalyzed cross-coupling of vinylsiloxanes with bromoalkynes: Synthesis of enynes. Organic Letters, 16(11), 3024-3027. https://doi.org/10.1021/ol501140p (Original work published 2014)