硫醇s -三氟甲基化的无金属光氧化还原催化

IF 2.3 4区化学 Q3 CHEMISTRY, PHYSICAL Catalysis Letters Pub Date : 2024-12-12 DOI:10.1007/s10562-024-04860-2

Raheemat Rafiu, Puspa Aryal, V. Prakash Reddy

{"title":"硫醇s -三氟甲基化的无金属光氧化还原催化","authors":"Raheemat Rafiu, Puspa Aryal, V. Prakash Reddy","doi":"10.1007/s10562-024-04860-2","DOIUrl":null,"url":null,"abstract":"<div><p>The <i>S</i>-trifluoromethylation of thiols is accomplished using a simple and cost-effective organic catalyst (diacetyl) along with a bench-stable and environmentally friendly trifluoromethylating reagent (Langlois reagent). Under optimized conditions (2.5 equivalents of Langlois reagent, Blue LED irradiation, 48-h reaction time at room temperature), the reaction yielded up to 81% <i>S</i>-trifluoromethylated product. This method’s high yields, compatibility with a broad substrate scope (aliphatic, heteroaromatic, and aromatic thiols), and environmentally friendly conditions demonstrate its potential for broader synthetic applications. In contrast to traditional methods that rely on organometallic catalysts and environmentally hazardous reagents, this novel photoredox catalysis method offers a more economical and sustainable alternative for <i>S</i>-trifluoromethylation of thiols.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":508,"journal":{"name":"Catalysis Letters","volume":"155 1","pages":""},"PeriodicalIF":2.3000,"publicationDate":"2024-12-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Metal-Free Photoredox Catalysis for the S-Trifluoromethylation of Thiols\",\"authors\":\"Raheemat Rafiu, Puspa Aryal, V. Prakash Reddy\",\"doi\":\"10.1007/s10562-024-04860-2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The <i>S</i>-trifluoromethylation of thiols is accomplished using a simple and cost-effective organic catalyst (diacetyl) along with a bench-stable and environmentally friendly trifluoromethylating reagent (Langlois reagent). Under optimized conditions (2.5 equivalents of Langlois reagent, Blue LED irradiation, 48-h reaction time at room temperature), the reaction yielded up to 81% <i>S</i>-trifluoromethylated product. This method’s high yields, compatibility with a broad substrate scope (aliphatic, heteroaromatic, and aromatic thiols), and environmentally friendly conditions demonstrate its potential for broader synthetic applications. In contrast to traditional methods that rely on organometallic catalysts and environmentally hazardous reagents, this novel photoredox catalysis method offers a more economical and sustainable alternative for <i>S</i>-trifluoromethylation of thiols.</p><h3>Graphical Abstract</h3>\\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":508,\"journal\":{\"name\":\"Catalysis Letters\",\"volume\":\"155 1\",\"pages\":\"\"},\"PeriodicalIF\":2.3000,\"publicationDate\":\"2024-12-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Catalysis Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10562-024-04860-2\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Catalysis Letters","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10562-024-04860-2","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

摘要

硫醇的s -三氟甲基化是使用一种简单且具有成本效益的有机催化剂（二乙酰基）和一种稳定且环保的三氟甲基化试剂（朗格卢瓦试剂）完成的。在优化条件下（2.5当量朗格卢瓦试剂，蓝光LED照射，室温下反应48 h）， s -三氟甲基化产物收率高达81%。该方法的产率高，与广泛的底物范围（脂肪族，杂芳烃和芳香族硫醇）的相容性，以及环境友好的条件表明其具有更广泛的合成应用潜力。与依赖有机金属催化剂和环境有害试剂的传统方法相比，这种新型光氧化还原催化方法为硫醇的s -三氟甲基化提供了一种更经济、更可持续的替代方法。图形抽象

本文章由计算机程序翻译，如有差异，请以英文原文为准。

摘要图片

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Metal-Free Photoredox Catalysis for the S-Trifluoromethylation of Thiols

The S-trifluoromethylation of thiols is accomplished using a simple and cost-effective organic catalyst (diacetyl) along with a bench-stable and environmentally friendly trifluoromethylating reagent (Langlois reagent). Under optimized conditions (2.5 equivalents of Langlois reagent, Blue LED irradiation, 48-h reaction time at room temperature), the reaction yielded up to 81% S-trifluoromethylated product. This method’s high yields, compatibility with a broad substrate scope (aliphatic, heteroaromatic, and aromatic thiols), and environmentally friendly conditions demonstrate its potential for broader synthetic applications. In contrast to traditional methods that rely on organometallic catalysts and environmentally hazardous reagents, this novel photoredox catalysis method offers a more economical and sustainable alternative for S-trifluoromethylation of thiols.

Graphical Abstract

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

Catalysis Letters 化学-物理化学

CiteScore

5.70

自引率

3.60%

发文量

327

审稿时长

1 months

期刊介绍： Catalysis Letters aim is the rapid publication of outstanding and high-impact original research articles in catalysis. The scope of the journal covers a broad range of topics in all fields of both applied and theoretical catalysis, including heterogeneous, homogeneous and biocatalysis. The high-quality original research articles published in Catalysis Letters are subject to rigorous peer review. Accepted papers are published online first and subsequently in print issues. All contributions must include a graphical abstract. Manuscripts should be written in English and the responsibility lies with the authors to ensure that they are grammatically and linguistically correct. Authors for whom English is not the working language are encouraged to consider using a professional language-editing service before submitting their manuscripts.