Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes
Hai N. Tran, Levi M. Stanley
Abstract
The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.
Topics & Concepts
HydroborationChemistryTransmetalationEnantioselective synthesisCatalysisAnhydrousNickelYield (engineering)Organic chemistryHydrideCombinatorial chemistryMetalMaterials scienceMetallurgyOrganoboron and organosilicon chemistryAsymmetric Hydrogenation and CatalysisCoordination Chemistry and Organometallics