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Issue 19, 2019
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Palladium-catalyzed double-bond migration of unsaturated hydrocarbons accelerated by tantalum chloride

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Abstract

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.

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

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Publication details

The article was received on 09 Jan 2019, accepted on 06 Feb 2019 and first published on 07 Feb 2019


Article type: Communication
DOI: 10.1039/C9CC00223E
Citation: Chem. Commun., 2019,55, 2769-2772

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

    M. Murai, K. Nishimura and K. Takai, Chem. Commun., 2019, 55, 2769
    DOI: 10.1039/C9CC00223E

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