Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.
A palladium-catalyzed three-component coupling of α-olefins, aryldiazonium salts, and bis(pinacolato)diboron affords direct access to chiral benzylic boronic esters. This process is rendered highly enantioselective using an unprecedented example of cooperative chiral anion phase transfer and transition-metal catalysis.
Department of Chemistry, University of California, Berkeley, California 94720, United States; Chemical Sciences Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States.
Hosea M
HM
Nelson
Department of Chemistry, University of California, Berkeley, California 94720, United States; Chemical Sciences Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States.
Brett D
BD
Williams
Department of Chemistry, University of California, Berkeley, California 94720, United States; Chemical Sciences Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States.
Javier
J
Miró
Department of Chemistry, University of California, Berkeley, California 94720, United States; Chemical Sciences Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States.
F Dean
FD
Toste
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D000838:Anions; D001896:Boron Compounds; D004952:Esters; D010165:Palladium