CuH-Catalyzed Reductive Coupling of Nitroarenes with Phosphine Oxides for the Direct Synthesis of Phosphamides
Jie Tang, Zhiyou Li, Qi Meng, Long Liu, Tianzeng Huang, Chunya Li, Qiang Li, Tieqiao Chen
Abstract
A CuH-catalyzed reductive coupling of nitroarenes with phosphine oxides is developed, which produces a series of phosphamides in moderate to excellent yields with good functional group tolerance. Gram-scale synthesis and late-stage modification of nitro-aromatic functional molecule niclosamide are also successfully conducted. The mechanism study shows that the nitro group is transformed after being reduced to nitroso and a nucleophilic addition procedure is involved during the reaction.
Topics & Concepts
ChemistryPhosphineNitroCatalysisCombinatorial chemistryNucleophileFunctional groupPhosphine oxideReductive eliminationNitrosoMedicinal chemistryOrganic chemistryAlkylPolymerNanomaterials for catalytic reactionsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis