2023ChemRxivOpen access

Practical Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioe-ster Derivatives

Gurupada Hazra, Ahmad Masarwa

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Abstract

Herein, we report a straightforward 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.

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Herein, we report a straightforward 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.

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Available abstract

Herein, we report a straightforward 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.

Key concepts: Thioether, Thioester, Surface modification, Combinatorial chemistry, Chemistry, Organic chemistry, Physical chemistry, Enzyme

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Practical Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioe-ster Derivatives — Research Paper | ScholarLens