title: Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.
abstract: Stereospecific coupling of benzylic carbamates and pivalates with aryl- and heteroarylboronic esters has been developed. The reaction proceeds with selective inversion or retention at the electrophilic carbon, depending on the nature of the ligand. Tricyclohexylphosphine ligand provides the product with retention, while an N-heterocyclic carbene ligand provides the product with inversion.
authors: Department of Chemistry, 4114 Natural Sciences 1, University of California, Irvine, California 92697, United States.
authors: Michael R
authors: MR
authors: Harris
authors: Luke E
authors: LE
authors: Hanna
authors: Margaret A
authors: MA
authors: Greene
authors: Curtis E
authors: CE
authors: Moore
authors: Elizabeth R
authors: ER
authors: Jarvo
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001593:Benzyl Compounds; D001897:Boronic Acids; D002219:Carbamates; D004952:Esters; D009942:Organometallic Compounds; D009532:Nickel; D008697:Methane