Electrochemical phosphorothiolation and 1,4-S → C phospho-Fries rearrangement: controlled access to phosphorothiolated and mercapto-phosphono substituted indolizines†
Xiang Liu, Wenxuan Jiang, Changfeng Huang, Shaohong Ma, Qiong Wang and Hua Cao
{"title":"Electrochemical phosphorothiolation and 1,4-S → C phospho-Fries rearrangement: controlled access to phosphorothiolated and mercapto-phosphono substituted indolizines†","authors":"Xiang Liu, Wenxuan Jiang, Changfeng Huang, Shaohong Ma, Qiong Wang and Hua Cao","doi":"10.1039/D3QO01042B","DOIUrl":null,"url":null,"abstract":"<p >An unprecedented electrochemically regioselective C–H phosphorothiolation and S- to C-[1,4] phosphoryl migration involving indolizines, elemental sulfur, and H-phosphonates in an undivided cell has been developed. This strategy utilizes elemental sulfur as an odorless sulfur source, providing a new avenue for the formation of C(sp<small><sup>2</sup></small>)–S–P bonds under sustainable conditions. Various phosphorothiolated and mercapto-phosphono substituted indolizines were obtained <em>via</em> controllable electrochemical phosphorothiolation and a 1,4-S → C phospho-Fries rearrangement. Additionally, this is the first example of successive electrochemical phosphorothiolation and a 1,4-S → C phospho-Fries rearrangement.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 20","pages":" 5198-5204"},"PeriodicalIF":4.6000,"publicationDate":"2023-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2023/qo/d3qo01042b","RegionNum":1,"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
An unprecedented electrochemically regioselective C–H phosphorothiolation and S- to C-[1,4] phosphoryl migration involving indolizines, elemental sulfur, and H-phosphonates in an undivided cell has been developed. This strategy utilizes elemental sulfur as an odorless sulfur source, providing a new avenue for the formation of C(sp2)–S–P bonds under sustainable conditions. Various phosphorothiolated and mercapto-phosphono substituted indolizines were obtained via controllable electrochemical phosphorothiolation and a 1,4-S → C phospho-Fries rearrangement. Additionally, this is the first example of successive electrochemical phosphorothiolation and a 1,4-S → C phospho-Fries rearrangement.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
