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Mechanistic Insight...
Mechanistic Insights into the Pd-Catalyzed Direct Amination of Allyl Alcohols : Evidence for an Outer-sphere Mechanism Involving a Palladium Hydride Intermediate
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- Sawadjoon, Supaporn (author)
- Uppsala universitet,Syntetisk organisk kemi
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- Sjöberg, Per J R (author)
- Uppsala universitet,Analytisk kemi
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- Orthaber, Andreas (author)
- Uppsala universitet,Molekylär biomimetik
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- Matsson, Olle (author)
- Uppsala universitet,Fysikalisk-organisk kemi
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- Samec, Joseph S M (author)
- Uppsala universitet,Syntetisk organisk kemi
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(creator_code:org_t)
- 2014-01-08
- 2014
- English.
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In: Chemistry - A European Journal. - : Wiley. - 0947-6539 .- 1521-3765. ; 20:6, s. 1520-1524
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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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.
Subject headings
- NATURVETENSKAP -- Kemi -- Analytisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Analytical Chemistry (hsv//eng)
- NATURVETENSKAP -- Kemi -- Fysikalisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Physical Chemistry (hsv//eng)
Publication and Content Type
- ref (subject category)
- art (subject category)
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