The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

• Erika Bálint,
• Ádám Tajti,
• Anna Ádám,
• István Csontos,
• Konstantin Karaghiosoff,
• Mátyás Czugler,
• Péter Ábrányi-Balogh and
• György Keglevich

Beilstein J. Org. Chem. 2017, 13, 76–86, doi:10.3762/bjoc.13.10

• and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism

• was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair. Keywords: α-aryl-α-aminophosphine oxides; α-aryl-α-aminophosphonates; microwave; Pudovik reaction

• which a >P(O)H species is added on the double bond of imines [11][12][13][14]. In this article, the latter pathway is utilized for the synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides. In most cases, the additions were carried out in the presence of a catalyst and solvent. The