1507941-47-0Relevant academic research and scientific papers
Metal-free synthesis of 6-phosphorylated phenanthridines: Synthetic and mechanistic insights
No?l-Duchesneau, Ludovik,Lagadic, Elodie,Morlet-Savary, Fabrice,Lohier, Jean-Fran?ois,Chataigner, Isabelle,Breugst, Martin,Lalevée, Jacques,Gaumont, Annie-Claude,Lakhdar, Sami
, p. 5900 - 5903 (2016)
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.
6-phosphorylated phenanthridines from 2-isocyanobiphenyls via radical C-P and C-C bond formation
Zhang, Bo,Daniliuc, Constantin Gabriel,Studer, Armido
supporting information, p. 250 - 253 (2014/01/23)
A C-P bond and a C-C bond are formed in the synthesis of 6-phosphorylated phenanthridines starting with readily prepared 2-isocyanobiphenyls and commercially available P-radical precursors. The radical cascade reaction comprises addition of an oxidatively generated P-centered radical to the isonitrile functionality and subsequent homolytic aromatic substitution. Various 6-phosphorylated phenanthridines are formed in moderate to excellent yield. In contrast to the currently intensively investigated direct arene phosphorylation, the arene core is constructed with concomitant phosphorylation using this approach.
