Fang Yutong, Chen Songlin, Chang Li-Yuan
Sinopec Research Institute of Petroleum Processing Beijing 100089 China.
Department of Basics, Naval University of Engineering Wuhan 430030 Hubei China
RSC Adv. 2024 Jan 2;14(2):812-830. doi: 10.1039/d3ra07791h.
Diaryl and di-heteroaryl sulfides exist in the structure of many drugs and important biological compounds, also these compounds are well-known in medicinal chemistry due to important biological and pharmaceutical activities. Therefore, the development of novel, ecofriendly and efficient catalytic systems for the preparation of diaryl and di-heteroaryl sulfides is a very attractive and important challenge in organic synthesis. In this attractive methodology, we wish to introduce FeO-supported 3-amino-4-mercaptobenzoic acid copper complex (FeO@AMBA-CuI) nanomaterials as a novel and efficient magnetically recoverable catalyst for the preparation of heteroaryl-aryl and di-heteroaryl sulfides with high yields through reaction of heteroaryl halides with aryl or heteroaryl boronic acids and S as the sulfur source under ecofriendly conditions. This catalytic system was very efficient and practical for a diverse range of heteroaryl substrates including benzothiazole, benzoxazole, benzimidazole, oxadiazole, benzofuran, and imidazo[1,2-]pyridine, because the desired diaryl and di-heteroaryl sulfides were prepared with high yields. The reusability-experiments revealed that the FeO@AMBA-CuI nanocatalyst can be magnetically separated and reused at least six times without a significant decrease in its catalytic activity. VSM and ICP-OES analyses confirmed that despite using the FeO@AMBA-CuI nanocatalyst 6 times, the magnetic properties and stability of the catalyst were still maintained. Although all the obtained heteroaryl-aryl and di-heteroaryl sulfide products are known and previously reported, the synthesis of this number of heteroaryl-aryl and di-heteroaryl sulfides has never been reported by any previouse methods.
二芳基和二杂芳基硫化物存在于许多药物和重要生物化合物的结构中，并且由于其重要的生物和药物活性，这些化合物在药物化学中也广为人知。因此，开发用于制备二芳基和二杂芳基硫化物的新型、环保且高效的催化体系是有机合成中一个非常有吸引力且重要的挑战。在这种引人注目的方法中，我们希望引入负载在FeO上的3-氨基-4-巯基苯甲酸铜配合物（FeO@AMBA-CuI）纳米材料，作为一种新型高效的可磁回收催化剂，用于在环保条件下通过杂芳基卤化物与芳基或杂芳基硼酸以及S作为硫源反应，高产率地制备杂芳基-芳基和二杂芳基硫化物。该催化体系对于包括苯并噻唑、苯并恶唑、苯并咪唑、恶二唑、苯并呋喃和咪唑并[1,2 - ]吡啶在内的多种杂芳基底物非常有效且实用，因为能高产率地制备出所需的二芳基和二杂芳基硫化物。可重复使用性实验表明，FeO@AMBA-CuI纳米催化剂可以通过磁性分离并至少重复使用六次，而其催化活性没有显著降低。VSM和ICP - OES分析证实，尽管FeO@AMBA-CuI纳米催化剂使用了6次，但其磁性和稳定性仍然得以保持。虽然所有得到的杂芳基-芳基和二杂芳基硫化物产物都是已知的且先前已有报道，但通过任何先前方法从未报道过如此数量的杂芳基-芳基和二杂芳基硫化物的合成。
