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Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation.

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.

SUBMITTER: Magre M

PROVIDER: S-EPMC7458426 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation.

Magre Marc M Paffenholz Eva E Maity Bholanath B Cavallo Luigi L Rueping Magnus M

Journal of the American Chemical Society 20200804 33

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. ...[more]

PMID: 32658463

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