title: Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides.
abstract: An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Suzuki
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Julie L
authors.initials: JL
authors.lastname: Hofstra
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Kelsey E
authors.identifier: 0000-0002-7446-257X
authors.initials: KE
authors.lastname: Poremba
authors.affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
authors.forename: Sarah E
authors.identifier: 0000-0001-8244-9300
authors.initials: SE
authors.lastname: Reisman
mesh_terms: D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D004952:Esters; D010797:Phthalimides; D014753:Vinyl Compounds; D009532:Nickel; C003763:vinyl bromide; C037437:N-hydroxyphthalimide