{"title":"Visible-Light-Promoted Thioetherification Reactions via Electron Donor-Acceptor Complexes between Active Esters and Sulfinates.","authors":"Xiao Xu,Qin-Hua Song","doi":"10.1021/acs.joc.5c00949","DOIUrl":null,"url":null,"abstract":"Visible-light-promoted thioetherification reactions occur via electron donor-acceptor (EDA) complexes between tetrachloro-N-hydroxyphthalimide esters (TCNHPI esters) and sulfinates. A series of alkyl aryl thioesters were obtained in yields of up to 85% across 38 cases. The measurement of association constant (KEDA = 584 M-1) shows very strong interaction in the EDA complex. The mechanism has been demonstrated by isolated byproducts, radical capture, UV/vis absorption, and fluorescence spectral measurements. The protocol provides a new facile approach for the synthesis of sulfides with odorless sulfinates in a mild condition.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"27 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-07-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c00949","RegionNum":2,"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
Visible-light-promoted thioetherification reactions occur via electron donor-acceptor (EDA) complexes between tetrachloro-N-hydroxyphthalimide esters (TCNHPI esters) and sulfinates. A series of alkyl aryl thioesters were obtained in yields of up to 85% across 38 cases. The measurement of association constant (KEDA = 584 M-1) shows very strong interaction in the EDA complex. The mechanism has been demonstrated by isolated byproducts, radical capture, UV/vis absorption, and fluorescence spectral measurements. The protocol provides a new facile approach for the synthesis of sulfides with odorless sulfinates in a mild condition.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.