title: Regioselective cross-coupling of allylboronic acid pinacol ester derivatives with aryl halides via Pd-PEPPSI-IPent.
abstract: The cross-coupling reactions of allylboronic acid pinacol ester derivatives with aryl and heteroaryl halides occurred with high selectivity (>97%) at the α-carbon of the allylboron reagent in the presence of Pd-PEPPSI-IPent precatalyst and 5 M KOH in refluxing THF. In the case of trisubstituted allylboronates with different substituents on the olefin, minor olefin geometry isomerization was observed (E/Z ≈ 80/20).
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, Canada M3J 1P3.
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Farmer
authors.forename: Howard N
authors.initials: HN
authors.lastname: Hunter
authors.forename: Michael G
authors.initials: MG
authors.lastname: Organ
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001897:Boronic Acids; D056831:Coordination Complexes; D004952:Esters; D006846:Hydrocarbons, Halogenated; D010636:Phenols