Xiaoran Feng, Zhaobo Liu, Qing-Yun Ni, Bing Wang, Michael J. Ingleson, Kang Yuan
{"title":"二炔烃的 N-定向双溴化反应使溴化 BN 嵌入多环芳烃成为可能","authors":"Xiaoran Feng, Zhaobo Liu, Qing-Yun Ni, Bing Wang, Michael J. Ingleson, Kang Yuan","doi":"10.1021/acs.orglett.4c03952","DOIUrl":null,"url":null,"abstract":"<i>N</i>-directed 2-fold bromoboration reactions of diynes with BBr<sub>3</sub> have been developed, allowing the access to novel internally BN-doped polycyclic aromatic hydrocarbons from readily available precursors under mild conditions. Computational investigations identified three potential reaction mechanisms, each involving either BBr<sub>3</sub> or [BBr<sub>4</sub>]<sup>−</sup>, with low activation barriers (<i>ΔG</i><sup><i>‡</i></sup> < 16 kcal/mol) for all pathways. The resulting brominated products can be further functionalized through various cross-coupling protocols, enabling the synthesis of highly luminescent emitters with quantum yield exceeding 90.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"N-Directed Two-Fold Bromoboration of Diynes Enables Access to Brominated BN-Embedded PAHs\",\"authors\":\"Xiaoran Feng, Zhaobo Liu, Qing-Yun Ni, Bing Wang, Michael J. Ingleson, Kang Yuan\",\"doi\":\"10.1021/acs.orglett.4c03952\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<i>N</i>-directed 2-fold bromoboration reactions of diynes with BBr<sub>3</sub> have been developed, allowing the access to novel internally BN-doped polycyclic aromatic hydrocarbons from readily available precursors under mild conditions. Computational investigations identified three potential reaction mechanisms, each involving either BBr<sub>3</sub> or [BBr<sub>4</sub>]<sup>−</sup>, with low activation barriers (<i>ΔG</i><sup><i>‡</i></sup> < 16 kcal/mol) for all pathways. The resulting brominated products can be further functionalized through various cross-coupling protocols, enabling the synthesis of highly luminescent emitters with quantum yield exceeding 90.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"14 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2024-11-20\",\"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.4c03952\",\"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://doi.org/10.1021/acs.orglett.4c03952","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
N-Directed Two-Fold Bromoboration of Diynes Enables Access to Brominated BN-Embedded PAHs
N-directed 2-fold bromoboration reactions of diynes with BBr3 have been developed, allowing the access to novel internally BN-doped polycyclic aromatic hydrocarbons from readily available precursors under mild conditions. Computational investigations identified three potential reaction mechanisms, each involving either BBr3 or [BBr4]−, with low activation barriers (ΔG‡ < 16 kcal/mol) for all pathways. The resulting brominated products can be further functionalized through various cross-coupling protocols, enabling the synthesis of highly luminescent emitters with quantum yield exceeding 90.
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.