title: Dehydrative cross-coupling reactions of allylic alcohols with olefins.
abstract: The direct dehydrative activation of allylic alcohols and subsequent cross-coupling with alkenes by using palladium catalyst containing a phosphoramidite ligand is described. The activation of the allyl alcohol does not require stoichiometric additives, thus allowing clean, waste-free reactions. The scope is demonstrated by application of the protocol to a series allylic alcohols and vinyl arenes, leading to variety of 1,4-diene products. Based on kinetic studies, a mechanism is proposed that involves a palladium hydride species that activates the allyl alcohol to form the allyl intermediate.
authors.affiliation: Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam (The Netherlands), Fax: (+31) 20 525 5604.
authors.forename: Yasemin
authors.initials: Y
authors.lastname: Gumrukcu
authors.forename: Bas
authors.initials: B
authors.lastname: de Bruin
authors.forename: Joost N H
authors.initials: JN
authors.lastname: Reek
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry
chemical_list: D000475:Alkenes; D020005:Propanols; D013343:Styrenes; C032391:palladium hydride; C006463:allyl alcohol; D010165:Palladium
keywords: alkenes; allylic alcohols; cross-coupling; palladium; phosphoramidite