Regiodivergent Hydroborative Ring Opening of Epoxides via Selec-tive C-O Bond Activation
Marc Magre, Eva Paffenholz, Bholanath Maity, Luigi Cavallo, Magnus Rueping
Journal of the American Chemical Society, (2020)
Regiodivergent Hydroborative, Selec-tive C-O Bond Activation
An unexpected magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epox-ides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mecha-nistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product for-mation.