Cobalt‐Catalyzed Regio‐ and Stereoselective Hydroboration of Allenes
Can Li, Zheng Yang, Lei Wang, Yinlong Guo, Zheng Huang, Shengming Ma
Abstract
An efficient pincer-ligand-based cobalt-complex-catalyzed allene hydroboration affording Z-allylic boronates is described. The reaction demonstrates an excellent regio- as well as Z-stereoselectivity and a wide substrate scope that tolerates many functional groups. Based on solvent-assisted electrospray ionization mass spectrometry (SAESI-MS) studies, a rationale for the cobalt-catalyzed hydroboration involving the highly selective insertion of an allene into the Co-H bond to form Z-allylic cobalt intermediates is proposed.
Topics & Concepts
HydroborationAlleneChemistryStereoselectivityCobaltAllylic rearrangementCatalysisLigand (biochemistry)Electrospray ionizationSubstrate (aquarium)Combinatorial chemistryStereochemistryOrganic chemistryMedicinal chemistryIonGeologyReceptorBiochemistryOceanographyOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods