Fei Chen, Gangqing Shi, Yang Zheng, Qinghao Dong, Wei Peng, Rentian Wang, Erjun Hao, Xin Wang, Kai Sun
{"title":"Three-Component Photochemical Cyclization/Dithiocarbamate Formation of <i>gem</i>-Difluoro Quinolin-2(1<i>H</i>)-ones.","authors":"Fei Chen, Gangqing Shi, Yang Zheng, Qinghao Dong, Wei Peng, Rentian Wang, Erjun Hao, Xin Wang, Kai Sun","doi":"10.1021/acs.orglett.4c03754","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, a novel visible-light-induced 6-<i>exo-trig</i> difluoromethylation cyclization and subsequent carbo-thioesterification reaction is described. This protocol allows efficient access to valuable <i>gem</i>-difluoro quinolin-2(1<i>H</i>)-ones in moderate to excellent yields under mild conditions. Broad amino sources compatibility, including cyclic morpholine, thiazolidine, thiomorpholine, pyrrolidine, 1,4-oxazepane, 2,6-dimethylmorpholine, <i>tert</i>-butyl piperazine-1-carboxylate and noncyclic diethylamine, <i>N</i>-ethylpropan-1-amine, <i>N</i>-benzylethanamine, <i>N</i>-benzyl-trimethylsilanamine, dibenzylamine, and <i>N</i>-(4-methoxybenzyl)ethanamine, demonstrated the practicability of this strategy. A radical-radical crossover route was proposed on the basis of radical inhibition experiments, visible light irradiation on-off test, apparent quantum efficiency (AQE) calculation, and fluorescence quenching studies.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-29","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.4c03754","RegionNum":1,"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
Abstract
Herein, a novel visible-light-induced 6-exo-trig difluoromethylation cyclization and subsequent carbo-thioesterification reaction is described. This protocol allows efficient access to valuable gem-difluoro quinolin-2(1H)-ones in moderate to excellent yields under mild conditions. Broad amino sources compatibility, including cyclic morpholine, thiazolidine, thiomorpholine, pyrrolidine, 1,4-oxazepane, 2,6-dimethylmorpholine, tert-butyl piperazine-1-carboxylate and noncyclic diethylamine, N-ethylpropan-1-amine, N-benzylethanamine, N-benzyl-trimethylsilanamine, dibenzylamine, and N-(4-methoxybenzyl)ethanamine, demonstrated the practicability of this strategy. A radical-radical crossover route was proposed on the basis of radical inhibition experiments, visible light irradiation on-off test, apparent quantum efficiency (AQE) calculation, and fluorescence quenching studies.
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.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
