title: 6-Phosphorylated phenanthridines from 2-isocyanobiphenyls via radical C-P and C-C bond formation.
abstract: 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.
authors: Institute of Organic Chemistry, Westfälische Wilhems-University , Corrensstraße 40, 48149 Münster, Germany.
authors: Bo
authors: B
authors: Zhang
authors: Constantin Gabriel
authors: CG
authors: Daniliuc
authors: Armido
authors: A
authors: Studer
mesh_terms: D001713:Biphenyl Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005609:Free Radicals / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D010766:Phosphorylation
chemical_list: D001713:Biphenyl Compounds; D005609:Free Radicals; D009570:Nitriles; D010617:Phenanthridines