title: Short Synthesis of Sulfur Analogues of Polyaromatic Hydrocarbons through Three Palladium-Catalyzed C-H Bond Arylations.
abstract: An expeditious synthesis of a wide range of phenanthro[9,10-b]thiophene derivatives, which are a class of polyaromatic hydrocarbon (PAH) containing a sulfur atom, is reported. The synthetic scheme involves only two operations from commercially available thiophenes, 2-bromobenzenesulfonyl chlorides and aryl bromides. In the first step, palladium-catalyzed desulfitative arylation using 2-bromobenzenesulfonyl chlorides allows the synthesis of thiophene derivatives, which are substituted at the C4 position by an aryl group containing an ortho-bromo substituent. Then, a palladium-catalyzed one-pot cascade intermolecular C5-arylation of thiophene using aryl bromides followed by intramolecular arylation led to the corresponding phenanthro[9,10-b]thiophenes in a single operation. In addition, PAHs containing two or three sulfur atoms, as well as both sulfur and nitrogen atoms, were also designed by this strategy.
authors.affiliation: Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 "Organométalliques, Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France.|Falculté des Sciences de Tunis, Université de Tunis El Manar , Campus Universitaire El-Manar, 2092 El Manar Tunis, Tunisia.|Laboratoire Physicochimie des Matériaux Minéraux et leurs Applications, Centre National des Recherches en Sciences des Matériaux , Technopole de Bordj Cedria, Soliman, 8027, Tunisia.
authors.forename: Wided
authors.initials: W
authors.lastname: Hagui
authors.affiliation: Laboratoire Physicochimie des Matériaux Minéraux et leurs Applications, Centre National des Recherches en Sciences des Matériaux , Technopole de Bordj Cedria, Soliman, 8027, Tunisia.
authors.forename: Néji
authors.initials: N
authors.lastname: Besbes
authors.affiliation: Laboratoire Physicochimie des Matériaux Minéraux et leurs Applications, Centre National des Recherches en Sciences des Matériaux , Technopole de Bordj Cedria, Soliman, 8027, Tunisia.
authors.forename: Ezzeddine
authors.initials: E
authors.lastname: Srasra
authors.affiliation: Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 "Organométalliques, Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France.
authors.forename: Thierry
authors.initials: T
authors.lastname: Roisnel
authors.affiliation: Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 "Organométalliques, Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Soulé
authors.affiliation: Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 "Organométalliques, Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France.
authors.forename: Henri
authors.initials: H
authors.lastname: Doucet