Construction and characterization of a magnetic nanoparticle-supported Cu complex: a stable and active nanocatalyst for synthesis of heteroaryl-aryl and di-heteroaryl sulfides

Abstract

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 Fe₃O₄-supported 3-amino-4-mercaptobenzoic acid copper complex (Fe₃O₄@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 S₈ 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-a]pyridine, because the desired diaryl and di-heteroaryl sulfides were prepared with high yields. The reusability-experiments revealed that the Fe₃O₄@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 Fe₃O₄@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.