title: Synthesis of E-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes.
abstract: The first Ni-catalyzed Suzuki-Miyaura coupling of alkyl halides with alkenyl-(9-BBN) reagents is reported. Both primary and secondary alkyl halides including alkyl chlorides can be coupled. The coupling method can be combined with hydroboration of terminal alkynes, allowing the expedited synthesis of functionalized alkyl alkenes from readily available alkynes with complete (E)-selectivity in one pot. The method was applied to the total synthesis of (±)-Recifeiolide, a natural macrolide.
authors.affiliation: Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne, Switzerland.
authors.forename: Thomas
authors.initials: T
authors.lastname: Di Franco
authors.affiliation: Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne, Switzerland.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Epenoy
authors.affiliation: Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne, Switzerland.
authors.forename: Xile
authors.initials: X
authors.lastname: Hu
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D000475:Alkenes; D000480:Alkynes; D003432:Cross-Linking Reagents; D006843:Hydrocarbons, Chlorinated; D007783:Lactones; C089339:recifeiolide; D009532:Nickel; C017573:nonane