title: Chemo- and stereoselective synthesis of fluorinated enamides from ynamides in HF/pyridine: second-generation approach to potent ureas bioisosteres.
abstract: (E)- and (Z)-α-fluoroenamides could be easily prepared with high levels of chemo- and regioselectivities by hydrofluorination of readily available ynamides with HF/pyridine. The scope and limitations of this new process for the hydrofluorination of ynamides, as well as the stability of the resulting α-fluoroenamides, have been extensively studied. Theoretical calculations at the MP2 and B3LYP levels of theory showed that the resulting fluoroenamides exhibit geometrical and electronic properties that partially mirror those of ureas, therefore demonstrating that the hydrofluorination of ynamides provides a general, straightforward, and user-friendly approach to bioisosteres of ureas, potent building blocks for biological studies and medicinal chemistry.
authors.affiliation: †Superacid Group in "Organic Synthesis" Team, Université de Poitiers, CNRS UMR 7285 IC2MP, Bât. B28, 4 rue Michel Brunet, TSA 51106, 86073 Poitiers Cedex 09, France.
authors.forename: Benoît
authors.initials: B
authors.lastname: Métayer
authors.affiliation: †Superacid Group in "Organic Synthesis" Team, Université de Poitiers, CNRS UMR 7285 IC2MP, Bât. B28, 4 rue Michel Brunet, TSA 51106, 86073 Poitiers Cedex 09, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Compain
authors.affiliation: ‡Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France.
authors.forename: Kévin
authors.initials: K
authors.lastname: Jouvin
authors.affiliation: †Superacid Group in "Organic Synthesis" Team, Université de Poitiers, CNRS UMR 7285 IC2MP, Bât. B28, 4 rue Michel Brunet, TSA 51106, 86073 Poitiers Cedex 09, France.
authors.forename: Agnès
authors.initials: A
authors.lastname: Martin-Mingot
authors.affiliation: §Computational Chemistry Group in "Catalysis and Renewable Carbon" Team, Université de Poitiers, CNRS UMR 7285 IC2MP, TSA 51106, 86073 Poitiers Cedex 09, France.
authors.forename: Christian
authors.initials: C
authors.lastname: Bachmann
authors.affiliation: ‡Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Marrot
authors.affiliation: ∥Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles, Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.
authors.forename: Gwilherm
authors.initials: G
authors.lastname: Evano
authors.affiliation: †Superacid Group in "Organic Synthesis" Team, Université de Poitiers, CNRS UMR 7285 IC2MP, Bât. B28, 4 rue Michel Brunet, TSA 51106, 86073 Poitiers Cedex 09, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Thibaudeau
mesh_terms: D002384:Catalysis; D004952:Esters; D054879:Halogenation; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry*
chemical_list: D004952:Esters; D011725:Pyridines; D014508:Urea; C023666:pyridine