Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride

Masahito Murai, Kengo Nishimura, Kazuhiko Takai

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl 5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylstyrenes through migration of up to a five-carbon chain. Both catalysts were commercially available, and the reaction occurred without external ligands under neutral conditions. The reaction proceeded via generation of π-allyl palladium species, which enabled the chemoselective double-bond migration of hydrocarbons in the presence of allylethers. Remote functionalization through double-bond migration was also demonstrated using FeCl 3 as a second catalyst.

Original languageEnglish
Pages (from-to)2769-2772
Number of pages4
JournalChemical Communications
Volume55
Issue number19
DOIs
Publication statusPublished - Jan 1 2019

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Palladium
Tantalum
Hydrocarbons
Catalysts
Functional groups
Carbon
Ligands
tantalum chloride

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride. / Murai, Masahito; Nishimura, Kengo; Takai, Kazuhiko.

In: Chemical Communications, Vol. 55, No. 19, 01.01.2019, p. 2769-2772.

Research output: Contribution to journalArticle

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