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

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.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-12-30
DOI
https://doi.org/10.1002/ejoc.202401222
Citations
2
Primary Topic
Synthesis of heterocyclic compounds
Type
article
Field-Weighted Citation Impact
0.50

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article

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

Hai‐Dong Xia, Xuan Li, Lihua Wen, Yubing Li et al.
2 citations
European Journal of Organic Chemistry
Synthesis of heterocyclic compounds
0.50
article

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

Hai‐Dong Xia, Xuan Li, Lihua Wen, Yubing Li, Mingyan Chen, Meng-Jun Xie
article en
2 citations

Abstract

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.

European Journal of Organic ChemistryVol. 28(6)
Shantou University (CN), Ji Hua Laboratory (CN), Key Laboratory of Guangdong Province (CN)
National Natural Science Foundation of China, Basic and Applied Basic Research Foundation of Guangdong Province
Openalex Percentile: Top 37%
Synthesis of heterocyclic compounds
0.50
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Multicomponent Modular Synthesis of Thioacetals by Using Dichloromethane as the C1 Synthon Under Mild Conditions — Hai‐Dong Xia, Xuan Li, et al. · European Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS