Study On The Synthesis Of S-aryl Phosphinothioates

The phosphinothioates, sulfur-contained organophosphorus compounds, are increasingly widely used in organic synthesis,pharmacochemistry and agrochemistry. The synthesis about this kind of functional organophosphorus compounds had gradually became hot research in the field of organic chemistry. The choice of a suitable method for the P-S-C bond formation was the key factor to achieve these compounds. We now reported a general method to prepare phosphinothioates through reductive coupling reaction of diphenylphosphine oxide with aryl/alkyl sulfonyl chlorides. Importantly, this approach is simple and the reactions could be carried out under metal- and base-free conditions. Under the optimized reaction conditions,the corresponding of S-aryl or S-alkyl 'phosphinothioates were obtained in good to excellent yield. In addition, this method can be .easily applied to gram-scale preparation. A proposed free radical reaction mechanism was outlined based on the radical trapping experiments and the model reaction monitored by 31P NMR spectroscopy. A simple synthesis of S-aryl phosphinothioates under L-proline's regulation in aqueous phase was also explored.