通过炔烃和光激发硝基烯烃的脱羰基缩合合成无金属和光催化剂的酰胺。

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-04 Epub Date: 2024-09-24 DOI:10.1021/acs.orglett.4c02513

Rongqi Cui, Qian Liao, Yuanxia Zhao, Lifang Wang, Yongqiang Zhang, Shuyang Liu, Ziyu Gan, Yufei Chen, Yi Shi, Lei Shi, Min Li, Yunhe Jin

{"title":"通过炔烃和光激发硝基烯烃的脱羰基缩合合成无金属和光催化剂的酰胺。","authors":"Rongqi Cui, Qian Liao, Yuanxia Zhao, Lifang Wang, Yongqiang Zhang, Shuyang Liu, Ziyu Gan, Yufei Chen, Yi Shi, Lei Shi, Min Li, Yunhe Jin","doi":"10.1021/acs.orglett.4c02513","DOIUrl":null,"url":null,"abstract":"Depending on the intrinsic photoactivity of nitroarenes, we herein developed a practical Brønsted acid-catalyzed decarbonylative amide synthesis from alkynes and photoexcited nitroarenes without any metal or photocatalyst. This method exhibited compatibility with water and air, broad substrate applicability, marvelous functional group tolerance, and wide applications in scale-up synthesis, late-stage functionalization, and total synthesis. Mechanism studies and DFT calculations supported that a 1,3,2-dioxazole intermediate was involved, and gaseous carbon monoxide was the only byproduct during amide construction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":"8222-8227"},"PeriodicalIF":4.9000,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Metal and Photocatalyst-Free Amide Synthesis via Decarbonylative Condensation of Alkynes and Photoexcited Nitroarenes.\",\"authors\":\"Rongqi Cui, Qian Liao, Yuanxia Zhao, Lifang Wang, Yongqiang Zhang, Shuyang Liu, Ziyu Gan, Yufei Chen, Yi Shi, Lei Shi, Min Li, Yunhe Jin\",\"doi\":\"10.1021/acs.orglett.4c02513\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Depending on the intrinsic photoactivity of nitroarenes, we herein developed a practical Brønsted acid-catalyzed decarbonylative amide synthesis from alkynes and photoexcited nitroarenes without any metal or photocatalyst. This method exhibited compatibility with water and air, broad substrate applicability, marvelous functional group tolerance, and wide applications in scale-up synthesis, late-stage functionalization, and total synthesis. Mechanism studies and DFT calculations supported that a 1,3,2-dioxazole intermediate was involved, and gaseous carbon monoxide was the only byproduct during amide construction.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\" \",\"pages\":\"8222-8227\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-10-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c02513\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/9/24 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c02513","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/24 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

根据硝基烯烃的内在光活性，我们在此开发了一种实用的布氏酸催化脱羰基酰胺合成方法，该方法由炔烃和光激发硝基烯烃组成，无需任何金属或光催化剂。该方法与水和空气相容，对底物的适用性广，对官能团的耐受性好，在放大合成、后期官能化和全合成方面应用广泛。机理研究和 DFT 计算证明，该方法涉及 1,3,2-二恶唑中间体，气态一氧化碳是生成酰胺过程中唯一的副产品。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Metal and Photocatalyst-Free Amide Synthesis via Decarbonylative Condensation of Alkynes and Photoexcited Nitroarenes.

查看原文本刊更多论文

Metal and Photocatalyst-Free Amide Synthesis via Decarbonylative Condensation of Alkynes and Photoexcited Nitroarenes.

Depending on the intrinsic photoactivity of nitroarenes, we herein developed a practical Brønsted acid-catalyzed decarbonylative amide synthesis from alkynes and photoexcited nitroarenes without any metal or photocatalyst. This method exhibited compatibility with water and air, broad substrate applicability, marvelous functional group tolerance, and wide applications in scale-up synthesis, late-stage functionalization, and total synthesis. Mechanism studies and DFT calculations supported that a 1,3,2-dioxazole intermediate was involved, and gaseous carbon monoxide was the only byproduct during amide construction.

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.