title: Eco-friendly solvents for palladium-catalyzed desulfitative C-H bond arylation of heteroarenes.
abstract: Herein, we report the Pd-catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross-coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions, the reaction proceeds with a wide range of heteroarenes. C2- or C5-arylated products were obtained with furan and pyrrole derivatives. Benzofuran was also arylated regioselectively at the C2-position, whereas the reaction proceeds selectively at the C3- or C4-positions if thiophenes and benzothiophenes are used. Moreover, in some cases, especially with 1-methylindole, solvent-free conditions afforded better regioselectivities and/or yields than the reaction performed in the presence of solvents.
authors.affiliation: Institut des Sciences Chimiques de Rennes, "Organométalliques, Matériaux et Catalyse", UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes (France).|Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène (UR 11ES56), Université de Monastir, Faculté des Sciences de Monastir, Avenue de l'environnement, Monastir 5000 (Tunisie).
authors.forename: Anoir
authors.initials: A
authors.lastname: Hfaiedh
authors.affiliation: Institut des Sciences Chimiques de Rennes, "Organométalliques, Matériaux et Catalyse", UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes (France).
authors.forename: Kedong
authors.initials: K
authors.lastname: Yuan
authors.affiliation: Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène (UR 11ES56), Université de Monastir, Faculté des Sciences de Monastir, Avenue de l'environnement, Monastir 5000 (Tunisie).
authors.forename: Hamed
authors.initials: H
authors.lastname: Ben Ammar
authors.affiliation: Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène (UR 11ES56), Université de Monastir, Faculté des Sciences de Monastir, Avenue de l'environnement, Monastir 5000 (Tunisie).
authors.forename: Bechir
authors.initials: B
authors.lastname: Ben Hassine
authors.affiliation: Institut des Sciences Chimiques de Rennes, "Organométalliques, Matériaux et Catalyse", UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes (France).
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Soulé
authors.affiliation: Institut des Sciences Chimiques de Rennes, "Organométalliques, Matériaux et Catalyse", UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes (France). henri.doucet@univ-rennes1.fr.
authors.forename: Henri
authors.initials: H
authors.lastname: Doucet
mesh_terms: D001572:Benzofurans / Q000737:chemistry; D002384:Catalysis; D004047:Diethyl Pyrocarbonate / Q000031:analogs & derivatives / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry
chemical_list: D001572:Benzofurans; D004987:Ethers; D007211:Indoles; D011758:Pyrroles; D012997:Solvents; D013450:Sulfones; D013876:Thiophenes; C017858:ethyl carbonate; D010165:Palladium; C022957:1-methylindole; C105430:benzofuran; D004047:Diethyl Pyrocarbonate; C010544:benzenesulfonyl chloride
keywords: arenes; cross-coupling; ch activation; palladium; solvent effects