title: Stereospecific Ni-catalyzed cross-coupling of potassium alkenyltrifluoroborates with alkyl halides.
abstract: A general method for the alkenylation of alkyl electrophiles using nearly stoichiometric amounts of the air- and moisture-stable potassium organotrifluoroborates has been developed. Various functional groups were tolerated on both the nucleophilic and electrophilic partner. Reactions of highly substituted E- and Z-alkenyltrifluoroborates, as well as vinyl- and propenyltrifluoroborates, were successful, and no loss of stereochemistry or regiochemistry was observed.
authors.affiliation: Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: O Andreea
authors.initials: OA
authors.lastname: Argintaru
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003432:Cross-Linking Reagents; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001881:Borates; D003432:Cross-Linking Reagents; D006843:Hydrocarbons, Chlorinated; D006845:Hydrocarbons, Fluorinated; D009532:Nickel; D011188:Potassium