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dc.contributor.authorMagre, Marc
dc.contributor.authorPaffenholz, Eva
dc.contributor.authorMaity, Bholanath
dc.contributor.authorCavallo, Luigi
dc.contributor.authorRueping, Magnus
dc.date.accessioned2020-08-17T05:48:00Z
dc.date.available2020-08-17T05:48:00Z
dc.date.issued2020-07-13
dc.date.submitted2020-05-31
dc.identifier.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
dc.identifier.issn0002-7863
dc.identifier.pmid32658463
dc.identifier.doi10.1021/jacs.0c05917
dc.identifier.urihttp://hdl.handle.net/10754/664617
dc.description.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.
dc.description.sponsorshipWe 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.
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/jacs.0c05917
dc.rightsThis is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
dc.rights.urihttp://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html
dc.titleRegiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation.
dc.typeArticle
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.contributor.departmentChemical Science Program
dc.identifier.journalJournal of the American Chemical Society
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen, Landoltweg 1, Aachen 52074, Germany
kaust.personMaity, Bholanath
kaust.personCavallo, Luigi
kaust.personRueping, Magnus
dc.date.accepted2020-07-13
refterms.dateFOA2020-08-17T05:48:29Z
kaust.acknowledged.supportUnitKAUST Supercomputing Laboratory
kaust.acknowledged.supportUnitsupercomputer Shaheen II
dc.date.published-online2020-07-13
dc.date.published-print2020-08-19


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