Issue 16, 2020

Direct synthesis of phosphorotrithioites and phosphorotrithioates from white phosphorus and thiols

Abstract

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.

Graphical abstract: Direct synthesis of phosphorotrithioites and phosphorotrithioates from white phosphorus and thiols

Supplementary files

Article information

Article type
Paper
Submitted
31 Kax 2019
Accepted
06 Qad 2020
First published
07 Qad 2020

Green Chem., 2020,22, 5303-5309

Direct synthesis of phosphorotrithioites and phosphorotrithioates from white phosphorus and thiols

X. Huangfu, Y. Wang, G. Lu, Y. Cao, G. Tang and Y. Zhao, Green Chem., 2020, 22, 5303 DOI: 10.1039/C9GC04452C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements