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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Palladium-Catalysed Desulfitative Heck Reaction-accepted.pdf (402.76 Ko)
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Palladium-Catalysed Desulfitative Heck Reaction_supporting information.pdf (6.45 Mo)
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Origin : Files produced by the author(s)
Origin : Files produced by the author(s)
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