title: Selective cross-coupling of organic halides with allylic acetates.
abstract: A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.
authors.affiliation: Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA.
authors.forename: Lukiana L
authors.initials: LL
authors.lastname: Anka-Lufford
authors.forename: Michael R
authors.initials: MR
authors.lastname: Prinsell
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Weix
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D005463:Fluoroacetates / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000081:Acetamides; D000085:Acetates; D000447:Aldehydes; D000498:Allyl Compounds; D005463:Fluoroacetates; D006219:Halogens; D007659:Ketones; D008024:Ligands; D013449:Sulfonamides; C030688:trifluoroacetamide; C498551:allyl acetate