Work

Multicomponent Modular Synthesis of Thioacetals by Using Dichloromethane as the C1 Synthon Under Mild Conditions

Year: 2024

Type: article

Abstract: Thioacetals are an important category of sulfur‐containing compounds and versatile building blocks. Therefore, there is growing demand for the development of practical and modular methods to access various thioacetals from inexpensive and readily available commodity chemicals. Herein, we describe a novel one‐pot multicomponent protocol for thioacetals synthesis, especially benzylthio thioacetals synthesis, by employing feedstock chemical dichloromethane (DCM) as the C1 source under metal‐free, mild and simple conditions. Furthermore, its synthetic utility is further demonstrated by the preparation of deuterated thioacetals, large‐scale synthesis and broad functional group compatibility. Preliminary mechanistic studies indicate the dual roles of DBU as both a proton scavenger and a nucleophilic catalyst. This work provides not only an excellent complementary strategy to the established thioacetals synthesis, but also a new platform for DCM application.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202401222

Authors: Meng‐Jun Xie, Li‐Hua Wen, Xuan Li, Ming‐Yan Chen, Yu‐Bing Li, Hai‐Dong Xia

Institutions: Shantou University, Key Laboratory of Guangdong Province

Language: English

Topic: Sulfur-Based Synthesis Techniques

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Basic and Applied Basic Research Foundation of Guangdong Province

Awards: G1708493511, G6604093606, G8469945727