title: Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions.
abstract: Stereospecific nickel-catalyzed cross-coupling reactions of benzylic 2-methoxyethyl ethers are reported for the preparation of enantioenriched 1,1-diarylethanes. The 2-methoxyethyl ether serves as a traceless directing group that accelerates cross-coupling. Chelation of magnesium ions is proposed to activate the benzylic C-O bond for oxidative addition.
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Greene
authors.forename: Ivelina M
authors.initials: IM
authors.lastname: Yonova
authors.forename: Florence J
authors.initials: FJ
authors.lastname: Williams
authors.forename: Elizabeth R
authors.initials: ER
authors.lastname: Jarvo
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D004980:Ethane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; D009532:Nickel; D004980:Ethane