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Multicomponent Modular Synthesis of Thioacetals by Using Dichloromethane as the C1 Synthon under Mild Conditions
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-12-31 , DOI: 10.1002/ejoc.202401222 Meng-Jun Xie, Li-Hua Wen, Xuan Li, Ming-Yan Chen, Yu-Bing Li, Hai-Dong Xia
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-12-31 , DOI: 10.1002/ejoc.202401222 Meng-Jun Xie, Li-Hua Wen, Xuan Li, Ming-Yan Chen, Yu-Bing Li, Hai-Dong Xia
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.
中文翻译:
在温和条件下以二氯甲烷作为 C1 合成子多组分模块化合成硫代缩醛
硫代缩醛是一类重要的含硫化合物和多功能结构单元。因此,对开发实用和模块化方法的需求不断增长,以便从廉价且容易获得的商品化学品中获得各种硫代缩醛。在本文中,我们通过在无金属、温和和简单的条件下采用原料化学二氯甲烷 (DCM) 作为 C1 源,描述了一种用于硫代缩醛合成的新型一锅多组分方案,特别是苄基硫代缩醛合成。此外,其合成效用通过制备氘代硫代缩醛、大规模合成和广泛的官能团相容性得到进一步证明。初步机理研究表明,DBU 既是质子清除剂又是亲核催化剂的双重作用。这项工作不仅为已建立的硫代缩醛合成提供了极好的补充策略,而且为 DCM 应用提供了新的平台。
更新日期:2024-12-31
中文翻译:
在温和条件下以二氯甲烷作为 C1 合成子多组分模块化合成硫代缩醛
硫代缩醛是一类重要的含硫化合物和多功能结构单元。因此,对开发实用和模块化方法的需求不断增长,以便从廉价且容易获得的商品化学品中获得各种硫代缩醛。在本文中,我们通过在无金属、温和和简单的条件下采用原料化学二氯甲烷 (DCM) 作为 C1 源,描述了一种用于硫代缩醛合成的新型一锅多组分方案,特别是苄基硫代缩醛合成。此外,其合成效用通过制备氘代硫代缩醛、大规模合成和广泛的官能团相容性得到进一步证明。初步机理研究表明,DBU 既是质子清除剂又是亲核催化剂的双重作用。这项工作不仅为已建立的硫代缩醛合成提供了极好的补充策略,而且为 DCM 应用提供了新的平台。