Highly Efficient One-Pot Synthesis of α-Aminophosphonates Catalyzed by Ytterbium Triflate in Water

Abstract

A facile one-pot, three-component synthesis of α -aminophosphonates catalyzed by ytterbium triflate [Yb(OTf)₃] in water using polyoxyethanyl α -tocopheryl sebacate (PTS) as amphiphile has been developed. The catalytic system could be readily recycled and reused several times without significant loss in its activity.

GRAPHICAL ABSTRACT

Keywords:

• α-Aminophosphonates
• micellar catalysis
• one-pot
• ytterbium triflate

Notes

^a Reaction conditions: benzaldehyde (1 mmol), aniline (1 mmol), diethyl phosphite (1.2 mmol), Yb(OTf)₃ (1 mol%), solvent (2 mL), additive (2 wt%), room temperature, 1 h.

^b Isolated yields.

^c 5 wt% of PTS was used.

^d Triton X-100 is polyethylene glycol octylphenol ether; SDS is sodium dodecyl sulfate; TBAB is tetrabutylammonium bromide.

^a Reaction conditions: benzaldehyde (1 mmol), aniline (1 mmol), diethyl phosphite (1.2 mmol), 2% PTS/H₂O (2 mL), room temperature, 1 h.

^b Isolated yields.

^a Reaction conditions: aldehyde (1 mmol), primary amine (1 mmol), diethyl phosphite (1.2 mmol), Yb(OTf)₃ (1 mol%), 2% PTS/H₂O (2 mL), room temperature, 1 h.

^b Isolated yields.

^c 5 mol% catalyst was used.