title: Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates.
abstract: We have developed a stereospecific, nickel-catalyzed cross-coupling of secondary benzylic ammonium salts and diboronate esters to deliver highly enantioenriched benzylic boronates. This reaction utilizes amine-derived electrophiles, which are readily available in high enantiopurity, and simple, inexpensive nickel catalysts. This reaction has broad scope, enabling synthesis of a variety of secondary benzylic boronates in good yields and excellent ee's.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Corey H
authors.initials: CH
authors.lastname: Basch
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Kelsey M
authors.initials: KM
authors.lastname: Cobb
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Mary P
authors.initials: MP
authors.lastname: Watson
mesh_terms: D064751:Ammonium Compounds / Q000737:chemistry*; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D064751:Ammonium Compounds; D001593:Benzyl Compounds; D001897:Boronic Acids; D009532:Nickel