Mn(III)-Mediated Radical Cyclization of <i>o</i>-Alkenyl Aromatic Isocyanides with Boronic Acids: Access to N-Unprotected 2-Aryl-3-cyanoindoles
Lu Liu, Lei Li, Xin Wang, Ran Sun, Mingdong Zhou, He Wang
Abstract
The synthesis of N-unprotected 2-aryl-3-cyanoindoles was realized via the Mn(III)-mediated radical cascade cyclization of o-alkenyl aromatic isocyanides with boronic acids. A possible mechanism involving a sequential intermolecular radical addition, intramolecular cyclization, and cleavage of the C–C bond under mild reaction conditions is proposed. Mechanism studies show that H2O or O2 might provide the oxygen source for the elimination of benzaldehyde.
Topics & Concepts
ChemistryArylIntramolecular forceRadicalIntermolecular forceBenzaldehydeMedicinal chemistryBond cleavageRadical cyclizationBoronic acidCombinatorial chemistryStereochemistryOrganic chemistryCatalysisMoleculeAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions