Triton-X-100 as an Organic Catalyst for One-Pot Synthesis of Arylmethyl-H-phosphinic Acids from Red Phosphorus and Arylmethyl Halides in the KOH/H2O/Toluene Multiphase Superbase System

Triton-X-100, a polyethylene glycol 4-(tert-octyl)phenyl ether, has been found to be an active micellar organic catalyst for the one-pot selective synthesis of arylmethyl-H-phosphinic acids in up 65% yields by direct phosphinylation arylmethyl halides with red phosphorus KOH/H2O/toluene multiphase superbase system. The demonstrates good recyclability. As result, expeditious method chemoselective acids—versatile sought-after organophosphorus compounds—has developed. is implemented via alkylation/oxidation halides, promoted hydroxide anions using Triton-X-100 (a commercial off-the-shelf recyclable catalyst). reaction comprises anions-assisted disassembly Pred 3D polymer molecules triggered separation from potassium cation ordinary crown-like micelles produce polyphosphide aqueous phase. Further, are alkylated phase presence catalytic reverse and species undergo double hydroxylation. advantages strategy developed include chemoselectivity, benign accessible starting reagents, recyclability, facile implementation.