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

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

The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 as a second catalyst greatly enhanced the migration efficiency to provide β-alkylstyrenes through migration of up to a five-carbon chain. Bo...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2019-02, Vol.55 (19), p.2769-2772
Hauptverfasser: Murai, Masahito, Nishimura, Kengo, Takai, Kazuhiko
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Catalysts
Ferric chloride
Functional groups
Hydrocarbons
Iron chlorides
Migration
NMR
Nuclear magnetic resonance
Palladium
Tantalum
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creator Murai, Masahito
Nishimura, Kengo
Takai, Kazuhiko
description The operationally simple palladium-catalyzed double-bond migration without heteroatom-containing coordinating functional groups is described. Addition of TaCl5 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 FeCl3 as a second catalyst.
doi_str_mv 10.1039/c9cc00223e
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Catalysis
Catalysts
Ferric chloride
Functional groups
Hydrocarbons
Iron chlorides
Migration
NMR
Nuclear magnetic resonance
Palladium
Tantalum
title Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride
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