Palladium-Catalysed Desulfitative Heck Reaction Tolerant to Aryl Carbon-Halogen Bonds for Access to (Poly)halo-Substituted Stilbene or Cinnamate Derivatives - Archive ouverte HAL Access content directly
Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2016

Palladium-Catalysed Desulfitative Heck Reaction Tolerant to Aryl Carbon-Halogen Bonds for Access to (Poly)halo-Substituted Stilbene or Cinnamate Derivatives

Abstract

The palladium-catalysed desulfitative Heck type reaction of (poly)halo-substituted benzenesulfonyl chlorides with alkenes was investigated. Styrene or acrylates in the presence of bromo- or iodobenzenesulfonyl chlorides and a phosphine-free palladium catalyst were found to afford the expected β-arylated Heck type products with complete regio- and stereoselectivities. The reaction tolerates a variety of substituents on the halobenzenesulfonyl chloride. Moreover, no cleavage of the C-Br and C-I bonds was observed in the course of these reactions, allowing further transformations. Using 4-bromobenzenesulfonyl chloride as the central unit, consecutive desulfitative Heck type reaction followed by palladium-catalysed direct arylation allowed to prepare heteroarylated stilbene derivatives in only two steps.
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Origin : Files produced by the author(s)
Origin : Files produced by the author(s)
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Dates and versions

hal-01367223 , version 1 (10-10-2016)

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Aymen Skhiri, Ridha Ben Salem, Jean-François Soulé, Henri Doucet. Palladium-Catalysed Desulfitative Heck Reaction Tolerant to Aryl Carbon-Halogen Bonds for Access to (Poly)halo-Substituted Stilbene or Cinnamate Derivatives. Synthesis: Journal of Synthetic Organic Chemistry, 2016, 48 (18), pp.3097-3106. ⟨10.1055/s-0035-1560449⟩. ⟨hal-01367223⟩
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