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)

Keywords

Regiodivergent Hydroborative, Selec-tive C-O Bond Activation

Abstract

​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.

Code

https://doi.org/10.1021/jacs.0c05917

Sources

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