title: Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: efficient access to α-alkyl vinylarenes.
abstract: Branched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TFA)2/dmphen (TFA = trifluoroacetate, dmphen = 2,9-dimethyl-1,10-phenanthroline) and proceed efficiently at 45-60 °C under 1 atm of O2 without requiring other additives. A broad array of functional groups, including aryl halide, allyl silane and carboxylic acids are tolerated.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706, USA. stahl@chem.wisc.edu.
authors.forename: Changwu
authors.initials: C
authors.lastname: Zheng
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006841:Hydrocarbons, Aromatic; D010165:Palladium; D010100:Oxygen