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Issue 9, 2018
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Palladium-catalysed coupling of α-halo vinylphosphonate and α-phosphonovinyl sulfonate with alkylzincs: straightforward and versatile synthesis of α-alkyl vinylphosphonates

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Abstract

With α-(pseudo)halo vinylphosphonate as the electrophilic coupling partner, a variety of alkyl- and benzylic zinc reagents underwent vinylation reactions to produce α-alkyl vinylphosphonates. This unprecedented Pd-catalysed Negishi coupling features mild reaction conditions, high functional group tolerance, broad substrate scope, retention of the olefin geometry, and easy gram-scale synthesis.

Graphical abstract: Palladium-catalysed coupling of α-halo vinylphosphonate and α-phosphonovinyl sulfonate with alkylzincs: straightforward and versatile synthesis of α-alkyl vinylphosphonates

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Publication details

The article was received on 08 Feb 2018, accepted on 01 Mar 2018 and first published on 01 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00156A
Citation: Org. Chem. Front., 2018,5, 1457-1461
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    Palladium-catalysed coupling of α-halo vinylphosphonate and α-phosphonovinyl sulfonate with alkylzincs: straightforward and versatile synthesis of α-alkyl vinylphosphonates

    L. Zhang, Y. Fang, X. Jin, T. Guo, R. Li, Y. Li, X. Li, Q. Ye and X. Luo, Org. Chem. Front., 2018, 5, 1457
    DOI: 10.1039/C8QO00156A

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