Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation.
KAUST DepartmentKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Chemical Science Program
Online Publication Date2020-07-13
Print Publication Date2020-08-19
Permanent link to this recordhttp://hdl.handle.net/10754/664617
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AbstractA 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.
CitationMagre, M., Paffenholz, E., Maity, B., Cavallo, L., & Rueping, M. (2020). Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C–O Bond Activation. Journal of the American Chemical Society. doi:10.1021/jacs.0c05917
SponsorsWe thank Frau Cornelia Vermeeren for preparative HPLC separation. The Deutsche Bundesstiftung Umwelt (DBU) is acknowledged for financial support for E. Paffenholz. We acknowledge the King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing computational resources of the supercomputer Shaheen II.
PublisherAmerican Chemical Society (ACS)
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