Palladium-catalyzed allylic alkylation of simple ketones with allylic alcohols and its mechanistic study

Xiaohong Huo, Guoqiang Yang, Delong Liu, Yangang Liu, Ilya Gridnev, Wanbin Zhang

Research output: Contribution to journalArticlepeer-review

112 Citations (Scopus)

Abstract

Allylic alcohols were directly used in Pd-catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20°C by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π-allylpalladium complex by lowering the activation barrier. Concerted action: Allylic alcohols were directly used in the title reaction under mild conditions. The reaction smoothly proceeds by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π-allylpalladium complex by lowering the activation barrier.

Original languageEnglish
Pages (from-to)6776-6780
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number26
DOIs
Publication statusPublished - 2014 Jun 23

Keywords

  • DFT calculation
  • allylic alcohol
  • allylic alkylation
  • organocatalysis
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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