Memory and dynamics in Pd-catalyzed allylic alkylation with P,N-ligands

Charlotte Johansson, Guy C. Lloyd-Jones, Per-Ola Norrby*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The memory effect, known to exert a strong influence on selectivity in some applications of the Pd-catalyzed allylic alkylation, has been investigated for a catalytic system based on a bidentate P,N-ligand. Although this system might be expected to show strong memory effects due to the difference in the trans influence of the two donor atoms (P > N), isotopic labeling revealed an almost complete absence of regio-retention. Modeling of dynamic processes in the intermediate (eta(3)-allyl)Pd complex allowed this observation to be rationalized in terms of anion-assisted apparent rotation. The study has allowed seemingly conflicting reports on the behavior of (eta(3)-allyl)Pd systems to be unified by a computational model. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1585-1592
Number of pages8
JournalTetrahedron: Asymmetry
Volume21
Issue number11-12
DOIs
Publication statusPublished - 23 Jun 2010

Keywords

  • CONTINUUM DIELECTRIC THEORY
  • ASYMMETRIC CATALYSIS
  • PALLADIUM(0) COMPLEXES
  • (ETA-3-ALLYL)PALLADIUM COMPLEXES
  • (PI-ALLYL)PALLADIUM COMPLEXES
  • SELECTIVE STABILIZATION
  • OXIDATIVE ADDITION
  • CHLORIDE-IONS
  • SUBSTITUTION
  • LIGANDS

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