title: Metal-Free Synthesis of 6-Phosphorylated Phenanthridines: Synthetic and Mechanistic Insights.
abstract: A novel and efficient method for the generation of phosphinoyl radicals from the combination of diphenyliodonium salt (Ph2I+,-OTf) with triethylamine (Et3N) in the presence of secondary phosphine oxides is reported. By employing this practical and simple approach, a large variety of 6-phosphorylated phenanthridines have been synthesized through the addition of phosphinoyl radicals to isonitriles as radical acceptors. The reaction works smoothly in the absence of any transition metal or photocatalyst. On the basis of electron paramagnetic resonance (EPR) and density functional theory (DFT) calculations, the mechanism of this reaction is discussed.
authors.affiliation: Normandie Université, LCMT, ENSICAEN, UNICAEN, CNRS , 6, Boulevard Maréchal Juin, Caen 14000 France.
authors.forename: Ludovik
authors.initials: L
authors.lastname: Noël-Duchesneau
authors.affiliation: Normandie Université, LCMT, ENSICAEN, UNICAEN, CNRS , 6, Boulevard Maréchal Juin, Caen 14000 France.
authors.forename: Elodie
authors.initials: E
authors.lastname: Lagadic
authors.affiliation: Institut de Science des Matériaux de Mulhouse IS2M - UMR CNRS 7361 - UHA , 15, rue Jean Starcky, Mulhouse 68057 Cedex, France.
authors.forename: Fabrice
authors.initials: F
authors.lastname: Morlet-Savary
authors.affiliation: Normandie Université, LCMT, ENSICAEN, UNICAEN, CNRS , 6, Boulevard Maréchal Juin, Caen 14000 France.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Lohier
authors.affiliation: Normandie Université, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014) , 76000 Rouen, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Chataigner
authors.affiliation: Department für Chemie, Universität zu Köln , Greinstraße 4, 50939 Köln, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Breugst
authors.affiliation: Institut de Science des Matériaux de Mulhouse IS2M - UMR CNRS 7361 - UHA , 15, rue Jean Starcky, Mulhouse 68057 Cedex, France.
authors.forename: Jacques
authors.initials: J
authors.lastname: Lalevée
authors.affiliation: Normandie Université, LCMT, ENSICAEN, UNICAEN, CNRS , 6, Boulevard Maréchal Juin, Caen 14000 France.
authors.forename: Annie-Claude
authors.initials: AC
authors.lastname: Gaumont
authors.affiliation: Normandie Université, LCMT, ENSICAEN, UNICAEN, CNRS , 6, Boulevard Maréchal Juin, Caen 14000 France.
authors.forename: Sami
authors.initials: S
authors.lastname: Lakhdar