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Mechanistic Insights into the Pd-Catalyzed Direct Amination of Allyl Alcohols: Evidence for an Outer-sphere Mechanism Involving a Palladium Hydride Intermediate
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Analytical Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
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2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 6, 1520-1524 p.Article in journal (Refereed) Published
Abstract [en]

The mechanism of direct amination of allyl alcohol by a palladium triphenylphosphite complex has been explored. Labelling studies show that the reaction proceeds through a π-allylpalladium intermediate. A second-order dependence of reaction rate on allyl alcohol concentration was observed. Kinetic isotope effect studies and ESI-MS studies are in agreement with a reaction proceeding through a palladium hydride intermediate in which both O-H bond and C-O bond cleavages are involved in rate-determining steps. A stereochemical study supports an outer-sphere nucleophilic attack of the π-allylpalladium intermediate giving complete chiral transfer from starting material to product.

Place, publisher, year, edition, pages
2014. Vol. 20, no 6, 1520-1524 p.
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Analytical Chemistry Physical Chemistry
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URN: urn:nbn:se:uu:diva-215613DOI: 10.1002/chem.201303431ISI: 000337300000008PubMedID: 24403056OAI: oai:DiVA.org:uu-215613DiVA: diva2:687799
Available from: 2014-01-15 Created: 2014-01-15 Last updated: 2017-12-06Bibliographically approved

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Sawadjoon, SupapornSjöberg, Per J ROrthaber, AndreasMatsson, OlleSamec, Joseph S M

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