Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation
Marc Magre, Eva Paffenholz, Bholanath Maity, Luigi Cavallo, Magnus Rueping
Abstract
A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.
Topics & Concepts
ChemistryHydroborationBond cleavageCatalysisRing (chemistry)StereochemistryMagnesiumRegioselectivityCombinatorial chemistryComputational chemistryOrganic chemistryChemical Synthesis and ReactionsOrganoboron and organosilicon chemistryAsymmetric Hydrogenation and Catalysis