Studies On The Chemoselective S-arylation Reaction Of Arynes With Indoline-2-thiones

The chemoselective S-arylation reactions of arynes and indoline-2-thiones bearing various substituents have been carried out.The reactive Kobayashi's aryne precursors successfully underwent S-arylation with thioamides with high chemoselectivities and up to 94%yield.This reaction provides an efficient synthesis toward 2-(arylthio)indolenines,a class of thioimidate compounds.In addition,the S-arylation of indoline-2-thiones in this protocol was also tolerable to other aryne precursors under base free conditions such as Hoye aryne precursor and benzenediazonium carboxylate.The potential synthetic utilities of our S-arylation method were supported by competition reaction experiments towards diversely functionalized additives,scale-up experiment,and as well as the derivatization of final thioimidate products.Moreover,it worth mentioning that the final thioimidate product remained stable under reduction conditions.