酰基自由基的均解芳取代:2-甲基喹啉与喹啉的氧化偶联

Journal of Chemical Research-s Pub Date : 2022-09-01 DOI:10.1177/17475198221126026

Xue Li, X. Wu, Jia Feng Yu, Yuanqing Zhang, Zhong Ke Hou, Yuanyuan Xie

{"title":"酰基自由基的均解芳取代:2-甲基喹啉与喹啉的氧化偶联","authors":"Xue Li, X. Wu, Jia Feng Yu, Yuanqing Zhang, Zhong Ke Hou, Yuanyuan Xie","doi":"10.1177/17475198221126026","DOIUrl":null,"url":null,"abstract":"Oxidative coupling of 2-methylquinolines with quinoxalines via a TBHP (t-butyl hydroperoxide) and TFA (trifluoroacetic acid) mediated Minisci reaction affords quinolin-2-yl(quinoxalin-2-yl)methanone derivatives. This approach provides a simple and efficient method to construct various acyl derivatives in moderate to good yields (45%–92%) without any metal catalyst. Mechanistically, homolytic aromatic substitution (HAS) of acyl radicals mediated by TBHP is crucial for the construction of the quinolin-2-yl(quinoxalin-2-yl)methanone products.","PeriodicalId":15318,"journal":{"name":"Journal of Chemical Research-s","volume":"31 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2022-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Homolytic aromatic substitution of acyl radicals: Oxidative coupling of 2-methylquinolines with quinoxalines\",\"authors\":\"Xue Li, X. Wu, Jia Feng Yu, Yuanqing Zhang, Zhong Ke Hou, Yuanyuan Xie\",\"doi\":\"10.1177/17475198221126026\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Oxidative coupling of 2-methylquinolines with quinoxalines via a TBHP (t-butyl hydroperoxide) and TFA (trifluoroacetic acid) mediated Minisci reaction affords quinolin-2-yl(quinoxalin-2-yl)methanone derivatives. This approach provides a simple and efficient method to construct various acyl derivatives in moderate to good yields (45%–92%) without any metal catalyst. Mechanistically, homolytic aromatic substitution (HAS) of acyl radicals mediated by TBHP is crucial for the construction of the quinolin-2-yl(quinoxalin-2-yl)methanone products.\",\"PeriodicalId\":15318,\"journal\":{\"name\":\"Journal of Chemical Research-s\",\"volume\":\"31 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2022-09-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Research-s\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1177/17475198221126026\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Research-s","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1177/17475198221126026","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}

引用次数: 0

摘要

2-甲基喹啉与喹诺啉通过TBHP (t-丁基过氧化氢)和TFA(三氟乙酸)介导的Minisci反应氧化偶联得到2-基(喹诺啉-2-基)甲烷酮衍生物。该方法在不需要任何金属催化剂的情况下，为构建各种酰基衍生物提供了一种简单有效的方法，产率为45% ~ 92%。从机理上看，三苯二酚介导的酰基自由基均溶性芳香取代(HAS)对喹啉-2-基(喹啉-2-基)甲烷产物的构建至关重要。

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

Homolytic aromatic substitution of acyl radicals: Oxidative coupling of 2-methylquinolines with quinoxalines

Oxidative coupling of 2-methylquinolines with quinoxalines via a TBHP (t-butyl hydroperoxide) and TFA (trifluoroacetic acid) mediated Minisci reaction affords quinolin-2-yl(quinoxalin-2-yl)methanone derivatives. This approach provides a simple and efficient method to construct various acyl derivatives in moderate to good yields (45%–92%) without any metal catalyst. Mechanistically, homolytic aromatic substitution (HAS) of acyl radicals mediated by TBHP is crucial for the construction of the quinolin-2-yl(quinoxalin-2-yl)methanone products.

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 Chemical Research-s 化学科学, 有机化学, 有机合成

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Chemical Research is a peer reviewed journal that publishes full-length review and research papers in all branches of experimental chemistry. The journal fills a niche by also publishing short papers, a format which favours particular types of work, e.g. the scope of new reagents or methodology, and the elucidation of the structure of novel compounds. Though welcome, short papers should not result in fragmentation of publication, they should describe a completed piece of work. The Journal is not intended as a vehicle for preliminary publications. The work must meet all the normal criteria for acceptance as regards scientific standards. Papers that contain extensive biological results or material relating to other areas of science may be diverted to more appropriate specialist journals. Areas of coverage include: Organic Chemistry; Inorganic Chemistry; Materials Chemistry; Crystallography; Computational Chemistry.