{"title":"Visible-Light-Induced α-Arylation of Ketones with (Hetero)aryl Halides","authors":"Chuyun Liang, Shuzhong Wang, Yunhao Xue, Xingyao He, Jialiang Qin, Ruoting Zhan, Bo Liu, Huicai Huang","doi":"10.1021/acs.orglett.4c03510","DOIUrl":null,"url":null,"abstract":"An enamine-mediated photoredox catalyzed C(sp<sup>2</sup>)–C(sp<sup>3</sup>) cross-coupling of dual radical precursors for the arylation of ketone is presented in this Letter. These reactions led to the formation of an enamine by using pyrrolidine to functionalize the C(sp<sup>3</sup>)–H bond in ketone substrates, which could be smoothly converted to α-arylated ketones with inert aryl bromides and even aryl chlorides in moderate to good yields under mild reaction conditions. The photocatalytically induced C(sp<sup>2</sup>)–C(sp<sup>3</sup>) cross-coupling between unactivated noncyclic ketones and aryl halides was achieved, and multiple carbonyl α-arylated backbones containing various natural products and drug molecules were successfully constructed.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"9 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-10-23","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.4c03510","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
An enamine-mediated photoredox catalyzed C(sp2)–C(sp3) cross-coupling of dual radical precursors for the arylation of ketone is presented in this Letter. These reactions led to the formation of an enamine by using pyrrolidine to functionalize the C(sp3)–H bond in ketone substrates, which could be smoothly converted to α-arylated ketones with inert aryl bromides and even aryl chlorides in moderate to good yields under mild reaction conditions. The photocatalytically induced C(sp2)–C(sp3) cross-coupling between unactivated noncyclic ketones and aryl halides was achieved, and multiple carbonyl α-arylated backbones containing various natural products and drug molecules were successfully constructed.
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.
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