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Mechanistic Insight...
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Sawadjoon, SupapornUppsala universitet,Syntetisk organisk kemi
(author)
Mechanistic Insights into the Pd-Catalyzed Direct Amination of Allyl Alcohols : Evidence for an Outer-sphere Mechanism Involving a Palladium Hydride Intermediate
- Article/chapterEnglish2014
Publisher, publication year, extent ...
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2014-01-08
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Wiley,2014
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printrdacarrier
Numbers
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LIBRIS-ID:oai:DiVA.org:uu-215613
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https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-215613URI
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https://doi.org/10.1002/chem.201303431DOI
Supplementary language notes
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Language:English
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Summary in:English
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Subject category:ref swepub-contenttype
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Subject category:art swepub-publicationtype
Notes
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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.
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Sjöberg, Per J RUppsala universitet,Analytisk kemi(Swepub:uu)psj18455
(author)
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Orthaber, AndreasUppsala universitet,Molekylär biomimetik(Swepub:uu)ortan368
(author)
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Matsson, OlleUppsala universitet,Fysikalisk-organisk kemi(Swepub:uu)oma05252
(author)
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Samec, Joseph S MUppsala universitet,Syntetisk organisk kemi(Swepub:uu)jossa512
(author)
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Uppsala universitetSyntetisk organisk kemi
(creator_code:org_t)
Related titles
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In:Chemistry - A European Journal: Wiley20:6, s. 1520-15240947-65391521-3765
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