{"title":"通过酸催化级联分子内 Friedel-Crafts 反应/重排/芳香化过程构建 2-取代的-3-芳基苯并呋喃和吲哚","authors":"Shaodong Liu, Qi Liu, Liang Cheng* and Li Liu*, ","doi":"10.1021/acs.joc.4c0149410.1021/acs.joc.4c01494","DOIUrl":null,"url":null,"abstract":"<p >We present here a new method for the synthesis of 2-substituted-3-aryl benzoheterocycles through a more challenging constrained [1,5]-type Friedel–Crafts reaction/rearrangement and aromatization process. By using the readily available 2-aryoxy-1,3-indandiones and 2-arylamino-1,3-indandiones, a range of 2-substituted-3-aryl benzofurans and indoles were prepared in good to excellent yields (yields up to 86%) under the catalysis of CF<sub>3</sub>SO<sub>3</sub>H or Sm(OTf)<sub>3</sub>. Compared with previous methods for constructing similar structures, this approach offers several advantages, including the use of easily accessible starting materials, mild reaction conditions, high yield, excellent regio- and diastereoselectivity, and a broad substrate scope.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"89 16","pages":"11716–11726 11716–11726"},"PeriodicalIF":3.6000,"publicationDate":"2024-07-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Construction of 2-Substituted-3-aryl Benzofurans and Indoles through an Acid-Catalyzed Cascade Intramolecular Friedel-Crafts Reaction/Rearrangement/Aromatization Process\",\"authors\":\"Shaodong Liu, Qi Liu, Liang Cheng* and Li Liu*, \",\"doi\":\"10.1021/acs.joc.4c0149410.1021/acs.joc.4c01494\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >We present here a new method for the synthesis of 2-substituted-3-aryl benzoheterocycles through a more challenging constrained [1,5]-type Friedel–Crafts reaction/rearrangement and aromatization process. By using the readily available 2-aryoxy-1,3-indandiones and 2-arylamino-1,3-indandiones, a range of 2-substituted-3-aryl benzofurans and indoles were prepared in good to excellent yields (yields up to 86%) under the catalysis of CF<sub>3</sub>SO<sub>3</sub>H or Sm(OTf)<sub>3</sub>. Compared with previous methods for constructing similar structures, this approach offers several advantages, including the use of easily accessible starting materials, mild reaction conditions, high yield, excellent regio- and diastereoselectivity, and a broad substrate scope.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"89 16\",\"pages\":\"11716–11726 11716–11726\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2024-07-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.4c01494\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.4c01494","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Construction of 2-Substituted-3-aryl Benzofurans and Indoles through an Acid-Catalyzed Cascade Intramolecular Friedel-Crafts Reaction/Rearrangement/Aromatization Process
We present here a new method for the synthesis of 2-substituted-3-aryl benzoheterocycles through a more challenging constrained [1,5]-type Friedel–Crafts reaction/rearrangement and aromatization process. By using the readily available 2-aryoxy-1,3-indandiones and 2-arylamino-1,3-indandiones, a range of 2-substituted-3-aryl benzofurans and indoles were prepared in good to excellent yields (yields up to 86%) under the catalysis of CF3SO3H or Sm(OTf)3. Compared with previous methods for constructing similar structures, this approach offers several advantages, including the use of easily accessible starting materials, mild reaction conditions, high yield, excellent regio- and diastereoselectivity, and a broad substrate scope.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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