title: Introduction of the 4,4,4-trifluorobut-2-ene chain exploiting a regioselective Tsuji-Trost reaction catalyzed by palladium nanoparticles.
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.
authors: Canada Research Chair in Organic and Medicinal Chemistry, CGCC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC G1V 0A6, Canada.
authors: Rémy
authors: R
authors: Hemelaere
authors: Canada Research Chair in Organic and Medicinal Chemistry, CGCC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC G1V 0A6, Canada.
authors: Justine
authors: J
authors: Desroches
authors: Canada Research Chair in Organic and Medicinal Chemistry, CGCC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC G1V 0A6, Canada.
authors: Jean-François
authors: JF
authors: Paquin