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

Marc Magre, Eva Paffenholz, Bholanath Maity, Luigi Cavallo, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

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.
Original languageEnglish (US)
JournalJournal of the American Chemical Society
DOIs
StatePublished - Jul 14 2020

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