3948-84-3Relevant articles and documents
Direct synthesis of phosphorotrithioites and phosphorotrithioates from white phosphorus and thiols
Cao, Yinwei,Huangfu, Xinlei,Lu, Guozhang,Tang, Guo,Wang, Yueqiao,Zhao, Yufen
supporting information, p. 5303 - 5309 (2020/09/17)
White phosphorus (P4) is still the major commercial P-atom source for the production of organophosphorus compounds. Conventionally, C-S-P bonds were constructed from environmentally questionable P(O)X directly or indirectly. From the green chemistry point of view, formation of C-S-P bonds from inorganic molecule P4 in an easy-to-operate and atom-economical way is essential because it will avoid the hazardous chlorination process. Only five methods for the formation of C-S-P bonds from P4 have been developed over the past 70 years. Here, the first general and high-yielding synthesis of P(SR)3 and P(O)(SR)3 involving P4 and thiols is presented. With the use of KOH or K2CO3 as a base and DMSO-toluene as a solvent, both arythiols and alkylthiols are tolerant in this transformation. The reaction is characterized by a complete conversion of white phosphorus. This operationally simple and environmentally sound reaction shows a broad scope of substrates and good functional group tolerance. Moreover, this method can be easily adapted to large-scale preparation.
