Kingkar Ghosh, Narendra Nath Ghosh, Prasun Choudhury, Subham Bhattacharjee, Rajat Saha, Mayukh Deb, Kinkar Biswas
{"title":"A benzimidazole-based Cu(II) complex catalyzed site-selective C-H sulfenylation of imidazo-[1,2-<i>a</i>]pyridines using CS<sub>2</sub> as a sulfur source.","authors":"Kingkar Ghosh, Narendra Nath Ghosh, Prasun Choudhury, Subham Bhattacharjee, Rajat Saha, Mayukh Deb, Kinkar Biswas","doi":"10.1039/d4ob00868e","DOIUrl":null,"url":null,"abstract":"<p><p>A new benzimidazole-based Cu(II) complex catalyzed site-selective sulfenylation of imidazo[1,2-<i>a</i>]pyridines with benzyl/alkyl/allyl bromides and CS<sub>2</sub> at 100 °C in DMF : H<sub>2</sub>O is reported. The present methodology has been developed for the synthesis of 3-sulfenyl imidazo[1,2-<i>a</i>]pyridines in good yields with a broad substrate scope. In this protocol, CS<sub>2</sub>, commonly known as a non-polar small molecule bioregulator (SMB), is converted to valuable sulfenylated imidazo[1,2-<i>a</i>]pyridine derivatives. In addition, theoretical investigations along with experimental evidence unfold the insights into the probable mechanistic pathway of site-selective sulfenylation from <i>S</i>,<i>S</i>-dibenzyltrithiocarbonate, which is particularly formed as an intermediate during the reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob00868e","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A new benzimidazole-based Cu(II) complex catalyzed site-selective sulfenylation of imidazo[1,2-a]pyridines with benzyl/alkyl/allyl bromides and CS2 at 100 °C in DMF : H2O is reported. The present methodology has been developed for the synthesis of 3-sulfenyl imidazo[1,2-a]pyridines in good yields with a broad substrate scope. In this protocol, CS2, commonly known as a non-polar small molecule bioregulator (SMB), is converted to valuable sulfenylated imidazo[1,2-a]pyridine derivatives. In addition, theoretical investigations along with experimental evidence unfold the insights into the probable mechanistic pathway of site-selective sulfenylation from S,S-dibenzyltrithiocarbonate, which is particularly formed as an intermediate during the reaction.