光催化分子内C-S键形成：2-取代苯并噻唑的绿色合成。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-16 DOI:10.1021/acs.joc.5c01090

Yuxuan Han,Zhe Lv,Xiaoting Chen,Yadong Feng,Xiuling Cui

{"title":"光催化分子内C-S键形成：2-取代苯并噻唑的绿色合成。","authors":"Yuxuan Han,Zhe Lv,Xiaoting Chen,Yadong Feng,Xiuling Cui","doi":"10.1021/acs.joc.5c01090","DOIUrl":null,"url":null,"abstract":"Visible-light-promoted oxidative cyclization reaction of thiobenzanilides for the intramolecular C-S bond construction has been developed. By employing acridinium salt as the photosensitizer, catalytic amount of tetramethylpiperidine-1-oxyl (TEMPO) as the hydrogen atom transfer (HAT) agent, and molecular oxygen from air as the terminal oxidant, 2-substituted benzothiazoles are efficiently synthesized under bases and transition metal-free conditions. A key feature of this transformation is that TEMPO as the HAT agent could be regenerated in the presence of molecular oxygen from air; this approach could tolerate various functional groups, offering a sustainable, environmentally benign photochemical pathway for the synthesis of benzothiazoles.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photocatalyzed Intramolecular C-S Bond Formation: Green Synthesis of 2-Substituted Benzothiazoles.\",\"authors\":\"Yuxuan Han,Zhe Lv,Xiaoting Chen,Yadong Feng,Xiuling Cui\",\"doi\":\"10.1021/acs.joc.5c01090\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Visible-light-promoted oxidative cyclization reaction of thiobenzanilides for the intramolecular C-S bond construction has been developed. By employing acridinium salt as the photosensitizer, catalytic amount of tetramethylpiperidine-1-oxyl (TEMPO) as the hydrogen atom transfer (HAT) agent, and molecular oxygen from air as the terminal oxidant, 2-substituted benzothiazoles are efficiently synthesized under bases and transition metal-free conditions. A key feature of this transformation is that TEMPO as the HAT agent could be regenerated in the presence of molecular oxygen from air; this approach could tolerate various functional groups, offering a sustainable, environmentally benign photochemical pathway for the synthesis of benzothiazoles.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"8 1\",\"pages\":\"\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-07-16\",\"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.5c01090\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.5c01090","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

摘要

研究了可见光促进的硫苯并苯胺类化合物的氧化环化反应，建立了分子内C-S键。以吖啶盐为光敏剂，以催化量的四甲基哌啶-1-氧（TEMPO）为氢原子转移（HAT）剂，以空气中的分子氧为末端氧化剂，在无碱和无过渡金属的条件下高效合成了2-取代苯并噻唑。这种转化的一个关键特征是，TEMPO作为HAT剂可以在空气中的分子氧存在下再生；该方法可耐受多种官能团，为苯并噻唑的合成提供了可持续、环保的光化学途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Photocatalyzed Intramolecular C-S Bond Formation: Green Synthesis of 2-Substituted Benzothiazoles.

Visible-light-promoted oxidative cyclization reaction of thiobenzanilides for the intramolecular C-S bond construction has been developed. By employing acridinium salt as the photosensitizer, catalytic amount of tetramethylpiperidine-1-oxyl (TEMPO) as the hydrogen atom transfer (HAT) agent, and molecular oxygen from air as the terminal oxidant, 2-substituted benzothiazoles are efficiently synthesized under bases and transition metal-free conditions. A key feature of this transformation is that TEMPO as the HAT agent could be regenerated in the presence of molecular oxygen from air; this approach could tolerate various functional groups, offering a sustainable, environmentally benign photochemical pathway for the synthesis of benzothiazoles.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

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.