title: Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C-N bond activation.
abstract: We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
authors.forename: Prantik
authors.initials: P
authors.lastname: Maity
authors.forename: Danielle M
authors.initials: DM
authors.lastname: Shacklady-McAtee
authors.forename: Glenn P A
authors.initials: GP
authors.lastname: Yap
authors.forename: Eric R
authors.initials: ER
authors.lastname: Sirianni
authors.forename: Mary P
authors.initials: MP
authors.lastname: Watson
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004980:Ethane / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D009942:Organometallic Compounds; D000644:Quaternary Ammonium Compounds; D012492:Salts; D009532:Nickel; D004980:Ethane