钯催化1-萘胺与二氯烷烃芳烃烷基化及其在熔融多环胺合成中的应用

IF 4.2 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemical Communications Pub Date : 2025-07-30 DOI:10.1039/d5cc03432a

Yixin Shi, Ziyi Zhou, Yilin Hu, Siyun Wang, Mingzhe Hong, Kai Cheng, Chunxiao Jia, Jie-Ping Wan

{"title":"钯催化1-萘胺与二氯烷烃芳烃烷基化及其在熔融多环胺合成中的应用","authors":"Yixin Shi, Ziyi Zhou, Yilin Hu, Siyun Wang, Mingzhe Hong, Kai Cheng, Chunxiao Jia, Jie-Ping Wan","doi":"10.1039/d5cc03432a","DOIUrl":null,"url":null,"abstract":"Herein, we report a palladium-catalyzed aromatic C-H bond alkylation reaction of 1-naphthylamines at the C8 site with dichloroalkanes as alkylating agents. DFT calculation demonstrates the distinctive advantage of the separated dichloroalkanes in the reaction by stabilizing key intermediate via C-H...N or C-H...π interaction induced by the additional Cl atom. In addition to the specific alkylation site selectivity in the naphthyl ring, the products provided by the current C-H alkylation protocol have displayed important application in the construction of fused polycyclic amines via one-step treatment.","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":"28 1","pages":""},"PeriodicalIF":4.2000,"publicationDate":"2025-07-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-catalyzed aromatic C-H alkylation of 1-naphthylamines with dichloroalkanes and the application in fused polycyclic amine synthesis\",\"authors\":\"Yixin Shi, Ziyi Zhou, Yilin Hu, Siyun Wang, Mingzhe Hong, Kai Cheng, Chunxiao Jia, Jie-Ping Wan\",\"doi\":\"10.1039/d5cc03432a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we report a palladium-catalyzed aromatic C-H bond alkylation reaction of 1-naphthylamines at the C8 site with dichloroalkanes as alkylating agents. DFT calculation demonstrates the distinctive advantage of the separated dichloroalkanes in the reaction by stabilizing key intermediate via C-H...N or C-H...π interaction induced by the additional Cl atom. In addition to the specific alkylation site selectivity in the naphthyl ring, the products provided by the current C-H alkylation protocol have displayed important application in the construction of fused polycyclic amines via one-step treatment.\",\"PeriodicalId\":67,\"journal\":{\"name\":\"Chemical Communications\",\"volume\":\"28 1\",\"pages\":\"\"},\"PeriodicalIF\":4.2000,\"publicationDate\":\"2025-07-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d5cc03432a\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5cc03432a","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

在此，我们报道了钯催化的芳香C-H键烷基化反应，在C8位点，以二氯烷烃为烷基化剂。DFT计算表明，通过C-H稳定关键中间体，分离出的二氯烷烃在反应中具有明显的优势。N或C-H…外加Cl原子诱导的π相互作用。目前的C-H烷基化方案所提供的产物除了在萘环上具有特定的烷基化位点选择性外，在一步法构建融合多环胺方面也显示出重要的应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Palladium-catalyzed aromatic C-H alkylation of 1-naphthylamines with dichloroalkanes and the application in fused polycyclic amine synthesis

Herein, we report a palladium-catalyzed aromatic C-H bond alkylation reaction of 1-naphthylamines at the C8 site with dichloroalkanes as alkylating agents. DFT calculation demonstrates the distinctive advantage of the separated dichloroalkanes in the reaction by stabilizing key intermediate via C-H...N or C-H...π interaction induced by the additional Cl atom. In addition to the specific alkylation site selectivity in the naphthyl ring, the products provided by the current C-H alkylation protocol have displayed important application in the construction of fused polycyclic amines via one-step treatment.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Chemical Communications 化学-化学综合

CiteScore

8.60

自引率

4.10%

发文量

2705

审稿时长

1.4 months

期刊介绍： ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.