Base‐Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines

Abstract

AbstractThe current protocol represents a transition metal‐free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2‐iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C−N bond formation followed by a radical C−C coupling in a cascade sequence. The used base potassium tert‐butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield.magnified image