Digging into the mechanism of oxidative Pd(II)-catalyzed aminations (Articolo in rivista)

Type
Label
  • Digging into the mechanism of oxidative Pd(II)-catalyzed aminations (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Alternative label
  • Lorion, Melanie M.; Nahra, Fady; Vu Linh Ly; Mealli, Carlo; Messaoudi, Abdelatif; Liron, Frederic; Oble, Julie; Poli, Giovanni (2014)
    Digging into the mechanism of oxidative Pd(II)-catalyzed aminations
    in Chimica oggi (Testo stamp.)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Lorion, Melanie M.; Nahra, Fady; Vu Linh Ly; Mealli, Carlo; Messaoudi, Abdelatif; Liron, Frederic; Oble, Julie; Poli, Giovanni (literal)
Pagina inizio
  • 30 (literal)
Pagina fine
  • 34 (literal)
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  • 32 (literal)
Rivista
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  • 5 (literal)
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  • 5 (literal)
Note
  • ISI Web of Science (WOS) (literal)
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  • University of Paris Sorbonne - Paris IV; Centre National de la Recherche Scientifique (CNRS); Consiglio Nazionale delle Ricerche (CNR) (literal)
Titolo
  • Digging into the mechanism of oxidative Pd(II)-catalyzed aminations (literal)
Abstract
  • Although the Pd(II)-catalyzed alkene aminopalladation and allylic C-H activation have been much described in literature, the in-depth mechanism of such type of process is far from being a simple matter. This account focuses on the oxidative intramolecular Pd(II)-catalyzed amination of unsaturated N-sulfonyl carbamates and carboxamides, revealing that different mechanistic paths can be operative. In particular, after activation of the unsaturation by Pd(II) catalyst, aminopalladation can take place, affording the corresponding high-energy cyclic (5- or 6-membered) aminopalladated intermediate (AmPI). This latter can evolve along different pathways, such as: distocyclic beta-H elimination, oxidation by a strong terminal oxidant, or carbopalladation. Otherwise, the cyclic AmPI can lay dormant, in equilibrium with the initial substrate. In this case, alternative reactivities may take place, such as allylic C-H activation of the olefinic substrate, [3,3]-sigmatropic rearrangement, or decomposition. (literal)
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