Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives

Herein, we report a straightforward practical method for efficiently obtaining a diverse range of thiophosphonium salts. This method involves the direct coupling of commercially available thiols and aldehydes with Ph3P and TfOH. The setup is simple and carried out in a metal-free manner. The synthetic utility of these salts is demonstrated through various examples of C-P bond functionalizations, enabling the synthesis of thioether, deuterated thioether, thioester, and dithioester derivatives. These products, which serve as valuable building blocks, are obtained in high yields.

Automated summary

Here, we present a simple and efficient method for obtaining a diverse range of thiophosphonium salts. This method involves the direct coupling of commercially available thiols and aldehydes with Ph3P and TfOH, without the need for metal catalysts. The synthesized salts demonstrate high synthetic utility through various examples of C-P bond functionalizations, enabling the synthesis of valuable building blocks in high yields.