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Introduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji–Trost Reaction Catalyzed by Palladium Nanoparticles

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journal contribution
posted on 03.04.2015, 00:00 by Rémy Hemelaere, Justine Desroches, Jean-François Paquin
A palladium-nanoparticle-catalyzed Tsuji–Trost reaction of 4,4,4-trifluorobut-2-en-1-yl acetate and ethyl­(4,4,4-trifluorobut-2-en-1-yl)­carbonate was accomplished with various nucleophiles including phenols, amines, and malonates. In the case of the phenols, isomerization of the double bond in the product (up to 20%) was observed as a side reaction. Further synthetic transformations including hydrogenation, the Diels–Alder reaction, and asymmetric dihydroxylation of a product were also examined.

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