Xueli Cui , Chunming Chen , Mei Xie , Taotao Zhao , Jianfeng Yi , Weiqiang Sun , Zhuang Xiong , Jinhui Hu , Wing-Leung Wong , Jia-Qiang Wu
{"title":"以二氯甲烷为 C1-质子,单锅顺序合成不对称的二芳基甲烷","authors":"Xueli Cui , Chunming Chen , Mei Xie , Taotao Zhao , Jianfeng Yi , Weiqiang Sun , Zhuang Xiong , Jinhui Hu , Wing-Leung Wong , Jia-Qiang Wu","doi":"10.1039/d4ob01158a","DOIUrl":null,"url":null,"abstract":"<div><div>Bisindolylmethane (BIM) and its derivatives are widely used in the pharmaceutical industry due to their significant biological activities. However, most reported synthetic methods are focused on the synthesis of symmetric BIMs, while the synthesis of unsymmetrical BIMs remains a challenge. Herein, an unprecedented two-step one-pot method to afford unsymmetrically substituted 3,3′-BIM frameworks, using methylene chloride (DCM) as the C1-synthon is reported. In this protocol, the formation of two C–C bonds can be achieved <em>via</em> a one-pot reaction. The utility of commercially available phenols and anilines was also demonstrated in the construction of unsymmetrical diarylmethanes. This protocol provides a straightforward approach to access diverse unsymmetrical diarylmethane derivatives under simple and mild conditions. The broad substrate compatibility and good functional group tolerance of the protocol support its practical application potential.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 39","pages":"Pages 7965-7970"},"PeriodicalIF":2.7000,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"One-pot sequential synthesis of unsymmetrical diarylmethanes using methylene chloride as a C1-synthon†\",\"authors\":\"Xueli Cui , Chunming Chen , Mei Xie , Taotao Zhao , Jianfeng Yi , Weiqiang Sun , Zhuang Xiong , Jinhui Hu , Wing-Leung Wong , Jia-Qiang Wu\",\"doi\":\"10.1039/d4ob01158a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Bisindolylmethane (BIM) and its derivatives are widely used in the pharmaceutical industry due to their significant biological activities. However, most reported synthetic methods are focused on the synthesis of symmetric BIMs, while the synthesis of unsymmetrical BIMs remains a challenge. Herein, an unprecedented two-step one-pot method to afford unsymmetrically substituted 3,3′-BIM frameworks, using methylene chloride (DCM) as the C1-synthon is reported. In this protocol, the formation of two C–C bonds can be achieved <em>via</em> a one-pot reaction. The utility of commercially available phenols and anilines was also demonstrated in the construction of unsymmetrical diarylmethanes. This protocol provides a straightforward approach to access diverse unsymmetrical diarylmethane derivatives under simple and mild conditions. The broad substrate compatibility and good functional group tolerance of the protocol support its practical application potential.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"22 39\",\"pages\":\"Pages 7965-7970\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-08-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024008103\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/9/6 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024008103","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/6 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
One-pot sequential synthesis of unsymmetrical diarylmethanes using methylene chloride as a C1-synthon†
Bisindolylmethane (BIM) and its derivatives are widely used in the pharmaceutical industry due to their significant biological activities. However, most reported synthetic methods are focused on the synthesis of symmetric BIMs, while the synthesis of unsymmetrical BIMs remains a challenge. Herein, an unprecedented two-step one-pot method to afford unsymmetrically substituted 3,3′-BIM frameworks, using methylene chloride (DCM) as the C1-synthon is reported. In this protocol, the formation of two C–C bonds can be achieved via a one-pot reaction. The utility of commercially available phenols and anilines was also demonstrated in the construction of unsymmetrical diarylmethanes. This protocol provides a straightforward approach to access diverse unsymmetrical diarylmethane derivatives under simple and mild conditions. The broad substrate compatibility and good functional group tolerance of the protocol support its practical application potential.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.