通过原位形成的 7-亚甲基-7H-吲哚炔基 1,6-共轭加成实现 β-萘酚的有机催化脱芳烃反应

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-01-07 DOI:10.1002/adsc.202401173

Shengfu Kang , Xiaohong Liu , Yi Zhang , Fang Fang , Wenjun Li , Pengfei Li

{"title":"通过原位形成的 7-亚甲基-7H-吲哚炔基 1,6-共轭加成实现 β-萘酚的有机催化脱芳烃反应","authors":"Shengfu Kang , Xiaohong Liu , Yi Zhang , Fang Fang , Wenjun Li , Pengfei Li","doi":"10.1002/adsc.202401173","DOIUrl":null,"url":null,"abstract":"<div><div>Organocatalytic dearomatization of β‐naphthols has been achieved via a 1,6‐conjugated addition of 2‐naphthols to alkynyl 7‐methylene‐7<em>H</em>‐indoles <em>in situ</em> generated from α‐(7‐indolyl)methanols. In the presence of racemic phosphoric acid, a series of tetrasubstituted allenes was obtained in high yields. Particularly, with the aid of chiral phosphoric acid, asymmetric dearomatization of β‐naphthols was investigated, affording axially chiral tetrasubstituted allenes with moderate enantioselectivity.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"367 1","pages":"Article e202401173"},"PeriodicalIF":4.4000,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Organocatalytic Dearomatization of β‐Naphthols through a 1,6‐Conjugated Addition of Alkynyl 7‐Methylene‐7H‐indoles Formed In Situ\",\"authors\":\"Shengfu Kang , Xiaohong Liu , Yi Zhang , Fang Fang , Wenjun Li , Pengfei Li\",\"doi\":\"10.1002/adsc.202401173\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Organocatalytic dearomatization of β‐naphthols has been achieved via a 1,6‐conjugated addition of 2‐naphthols to alkynyl 7‐methylene‐7<em>H</em>‐indoles <em>in situ</em> generated from α‐(7‐indolyl)methanols. In the presence of racemic phosphoric acid, a series of tetrasubstituted allenes was obtained in high yields. Particularly, with the aid of chiral phosphoric acid, asymmetric dearomatization of β‐naphthols was investigated, affording axially chiral tetrasubstituted allenes with moderate enantioselectivity.</div></div>\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"367 1\",\"pages\":\"Article e202401173\"},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2025-01-07\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1615415024006034\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1615415024006034","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

摘要

通过将 2-萘酚与由α-(7-吲哚基)甲醇原位生成的炔基 7-亚甲基-7H-吲哚进行 1,6-共轭加成，实现了 β-萘酚的有机催化脱芳烃。在外消旋磷酸存在下，可以高产率获得一系列四取代烯烃。特别是在手性磷酸的帮助下，研究了 β-萘酚的不对称脱芳烃作用，以中等对映选择性得到了轴向手性四取代烯烃。

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

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Organocatalytic Dearomatization of β‐Naphthols through a 1,6‐Conjugated Addition of Alkynyl 7‐Methylene‐7H‐indoles Formed In Situ

Organocatalytic dearomatization of β‐naphthols has been achieved via a 1,6‐conjugated addition of 2‐naphthols to alkynyl 7‐methylene‐7H‐indoles in situ generated from α‐(7‐indolyl)methanols. In the presence of racemic phosphoric acid, a series of tetrasubstituted allenes was obtained in high yields. Particularly, with the aid of chiral phosphoric acid, asymmetric dearomatization of β‐naphthols was investigated, affording axially chiral tetrasubstituted allenes with moderate enantioselectivity.

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.