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

Author:
Murai, Masahito, Nishimura, Kengo, Takai, Kazuhiko
Source:
Chemical communications 2019 v.55 no.19 pp. 2769-2772
ISSN:
1364-548X
Subject:
catalysts, catalytic activity, chemical bonding, chemical reactions, chemoselectivity, ferric chloride, hydrocarbons, ligands, moieties, palladium, tantalum
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.
Agid:
6322527