Ru(II)-催化[1,4]-异位重排和分子内协调SNAr的芳基和杂芳基硫代衍生物的醌类卡宾

IF 13.1 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-12-02 DOI:10.1021/acscatal.4c05272

Subarna Pan, Md. Saimuddin Sk, Bortika Sanyal, Lisa Roy, Rajarshi Samanta

{"title":"Ru(II)-催化[1,4]-异位重排和分子内协调SNAr的芳基和杂芳基硫代衍生物的醌类卡宾","authors":"Subarna Pan, Md. Saimuddin Sk, Bortika Sanyal, Lisa Roy, Rajarshi Samanta","doi":"10.1021/acscatal.4c05272","DOIUrl":null,"url":null,"abstract":"A Ru(II)-catalyzed straightforward and efficient strategy has been developed to construct O-alkylated arylnaphthyl thioether derivatives using arylthioacetates/arylalkylthioethers with diazonaphthoquinone via a [1,4]-oxa sigmatropic rearrangement. In a complementary method, heteroaryl thioacetate/heteroaryl alkylthioethers offer O-heteroaryl alkylnaphthyl thioether derivatives via an interesting concerted intramolecular SNAr-type reaction. Both of these methods proceed through the formation of Ru-based quinoid carbene and sulfur ylide, respectively. A detailed mechanistic study and DFT calculations reveal that the reaction is going via a concerted manner. Postsynthetic modifications of the synthesized compounds led to sulfur-containing polyaromatic heterocycles.","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"26 1","pages":""},"PeriodicalIF":13.1000,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ru(II)-Catalyzed [1,4]-Sigmatropic Rearrangement and Intramolecular Concerted SNAr of Aryl and Heteroarylthio Derivatives using Quinoid Carbene\",\"authors\":\"Subarna Pan, Md. Saimuddin Sk, Bortika Sanyal, Lisa Roy, Rajarshi Samanta\",\"doi\":\"10.1021/acscatal.4c05272\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A Ru(II)-catalyzed straightforward and efficient strategy has been developed to construct O-alkylated arylnaphthyl thioether derivatives using arylthioacetates/arylalkylthioethers with diazonaphthoquinone via a [1,4]-oxa sigmatropic rearrangement. In a complementary method, heteroaryl thioacetate/heteroaryl alkylthioethers offer O-heteroaryl alkylnaphthyl thioether derivatives via an interesting concerted intramolecular SNAr-type reaction. Both of these methods proceed through the formation of Ru-based quinoid carbene and sulfur ylide, respectively. A detailed mechanistic study and DFT calculations reveal that the reaction is going via a concerted manner. Postsynthetic modifications of the synthesized compounds led to sulfur-containing polyaromatic heterocycles.\",\"PeriodicalId\":9,\"journal\":{\"name\":\"ACS Catalysis \",\"volume\":\"26 1\",\"pages\":\"\"},\"PeriodicalIF\":13.1000,\"publicationDate\":\"2024-12-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Catalysis \",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acscatal.4c05272\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acscatal.4c05272","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

摘要

采用Ru（II）催化，通过[1,4]-氧基异位重排，以芳基硫乙酸酯/芳基烷基硫醚与重氮萘醌为原料，构建了一种直接高效的o -烷基化芳基萘硫醚衍生物。在一种互补的方法中，杂芳基硫乙酸酯/杂芳基烷基硫醚通过一个有趣的协同分子内snar型反应提供o -杂芳基烷基萘硫醚衍生物。这两种方法分别通过生成钌基类醌和硫酰。详细的机理研究和DFT计算表明，反应是通过协调方式进行的。合成化合物的合成后修饰导致含硫多芳杂环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Ru(II)-Catalyzed [1,4]-Sigmatropic Rearrangement and Intramolecular Concerted SNAr of Aryl and Heteroarylthio Derivatives using Quinoid Carbene

查看原文本刊更多论文

Ru(II)-Catalyzed [1,4]-Sigmatropic Rearrangement and Intramolecular Concerted SNAr of Aryl and Heteroarylthio Derivatives using Quinoid Carbene

A Ru(II)-catalyzed straightforward and efficient strategy has been developed to construct O-alkylated arylnaphthyl thioether derivatives using arylthioacetates/arylalkylthioethers with diazonaphthoquinone via a [1,4]-oxa sigmatropic rearrangement. In a complementary method, heteroaryl thioacetate/heteroaryl alkylthioethers offer O-heteroaryl alkylnaphthyl thioether derivatives via an interesting concerted intramolecular S_NAr-type reaction. Both of these methods proceed through the formation of Ru-based quinoid carbene and sulfur ylide, respectively. A detailed mechanistic study and DFT calculations reveal that the reaction is going via a concerted manner. Postsynthetic modifications of the synthesized compounds led to sulfur-containing polyaromatic heterocycles.

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

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.