Iodine-promoted direct thiolation (selenylation) of imidazole with disulfides (diselenide): A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazole

A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazoles from imidazoles and disulfides (diselenides) was developed through the direct thiolation (selenylation) of imidazoles promoted by 0.5 equiv. of iodine. This process is scalable and tolerates a wide spectrum of disulfides (diselenides) to deliver products in high yields. Compared with previous methods, this protocol has the advantages of a simple operation, wide functional group tolerance and good yields, providing an efficient route to 2-arylthio(seleno)imidazoles, which are key structural scaffolds of many natural products. (C) 2020 Elsevier Ltd. All rights reserved.