Pengfei Li, , , Fan Wu, , , Chulin Qu, , , Hidemitsu Uno*, , and , Zhen Shen*,
{"title":"两种阳离子反芳香族游离碱衍生物","authors":"Pengfei Li, , , Fan Wu, , , Chulin Qu, , , Hidemitsu Uno*, , and , Zhen Shen*, ","doi":"10.1021/acs.orglett.5c03111","DOIUrl":null,"url":null,"abstract":"<p >The synthesis of free-base antiaromatic porphyrinoids remains a challenging task. Herein we report the first preparation of two cationic free-base antiaromatic corroles, <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> (containing two NH moieties, slightly saddle-shaped) and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> (containing four NH moieties, severely distorted saddle-shaped), utilizing a strategy of β-annulated benzene rings to suppress side reactions. The antiaromatic character of <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> is robustly supported by crystallographic analysis, spectroscopic evidence, and theoretical calculations.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 39","pages":"10948–10953"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Two Cationic Antiaromatic Free-Base Corroles\",\"authors\":\"Pengfei Li, , , Fan Wu, , , Chulin Qu, , , Hidemitsu Uno*, , and , Zhen Shen*, \",\"doi\":\"10.1021/acs.orglett.5c03111\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The synthesis of free-base antiaromatic porphyrinoids remains a challenging task. Herein we report the first preparation of two cationic free-base antiaromatic corroles, <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> (containing two NH moieties, slightly saddle-shaped) and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> (containing four NH moieties, severely distorted saddle-shaped), utilizing a strategy of β-annulated benzene rings to suppress side reactions. The antiaromatic character of <b>BC(H</b><sub><b>2</b></sub><b>)</b><sup><b>+</b></sup> and <b>BC(H</b><sub><b>4</b></sub><b>)</b><sup><b>3+</b></sup> is robustly supported by crystallographic analysis, spectroscopic evidence, and theoretical calculations.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 39\",\"pages\":\"10948–10953\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-09-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03111\",\"RegionNum\":1,\"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":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03111","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
The synthesis of free-base antiaromatic porphyrinoids remains a challenging task. Herein we report the first preparation of two cationic free-base antiaromatic corroles, BC(H2)+ (containing two NH moieties, slightly saddle-shaped) and BC(H4)3+ (containing four NH moieties, severely distorted saddle-shaped), utilizing a strategy of β-annulated benzene rings to suppress side reactions. The antiaromatic character of BC(H2)+ and BC(H4)3+ is robustly supported by crystallographic analysis, spectroscopic evidence, and theoretical calculations.
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.