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Desulfitative Pd-catalysed coupling reaction using benzenesulfonyl chlorides and enones as the coupling partners.

Abstract : The reaction of benzenesulfonyl chlorides with enones was investigated. β-Ionone and benzalacetone in the presence of a palladium catalyst were found to afford the conjugate addn. products instead of the expected Heck type products. The reaction tolerates a wide variety of substituents on the benzenesulfonyl chloride. It should be noted that no cleavage of the C-Br and C-I bonds was obsd. in the course of the reactions with 4-bromo- or 4-iodobenzenesulfonyl chlorides, allowing further transformations. For example, using 4-bromobenzenesulfonyl chloride as the central unit, consecutive conjugate addn. and subsequent arylation allowed access to substituted bi(hetero)aryls.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01153408
Contributor : Laurent Jonchère <>
Submitted on : Tuesday, May 19, 2015 - 5:25:07 PM
Last modification on : Thursday, March 5, 2020 - 2:02:28 PM

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Kedong Yuan, Rui Sang, Jean-François Soulé, Henri Doucet. Desulfitative Pd-catalysed coupling reaction using benzenesulfonyl chlorides and enones as the coupling partners.. Catalysis Science & Technology, Royal Society of Chemistry, 2015, 5 (5), pp.2904--2912. ⟨10.1039/C5CY00089K⟩. ⟨hal-01153408⟩

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