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

Author:
Hemelaere, Rémy, Desroches, Justine, Paquin, Jean-François
Source:
Organic letters 2015 v.17 no.7 pp. 1770-1773
ISSN:
1523-7052
Subject:
Lewis bases, acetates, amines, chemical bonding, chemical structure, dihydroxylation, hydrogenation, isomerization, nanoparticles, palladium, phenols, regioselectivity
Abstract:
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.
Agid:
5790431