V–Catalyzed Direct Ortho‐Aminomethylation of Phenols

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-10-01 DOI:10.1002/ajoc.202400194
{"title":"V–Catalyzed Direct Ortho‐Aminomethylation of Phenols","authors":"","doi":"10.1002/ajoc.202400194","DOIUrl":null,"url":null,"abstract":"<div><div>A strategy for cross‐dehydrogenative C(sp2)‐C(sp3) coupling was developed by direct and highly selective V‐catalyzed ortho‐aminomethylation of phenol with aniline derivatives. A series of aminomethylphenol compounds were obtained in moderate to good yields under mild reaction conditions and with a broad substrate scope. A possible radical mechanism was proposed, and it was found that the coordination of phenolic hydroxyl groups with V<sup>5+</sup> was crucial for the effective activation of the ortho position.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 10","pages":"Article e202400194"},"PeriodicalIF":2.8000,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2193580724002733","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

A strategy for cross‐dehydrogenative C(sp2)‐C(sp3) coupling was developed by direct and highly selective V‐catalyzed ortho‐aminomethylation of phenol with aniline derivatives. A series of aminomethylphenol compounds were obtained in moderate to good yields under mild reaction conditions and with a broad substrate scope. A possible radical mechanism was proposed, and it was found that the coordination of phenolic hydroxyl groups with V5+ was crucial for the effective activation of the ortho position.
查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
V 催化苯酚的直接正氨甲基化反应
通过苯酚与苯胺衍生物直接和高选择性的 V 催化邻氨基甲基化反应,开发了一种 C(sp2)-C(sp3)交叉脱氢偶联策略。在温和的反应条件下,获得了一系列氨甲基苯酚化合物,收率从中等到良好,底物范围广泛。研究人员提出了一种可能的自由基机理,并发现酚羟基与 V5+ 的配位是有效激活正位的关键。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
期刊最新文献
TEMPO‐Mediated Cross‐Dehydrogenative Coupling for the Synthesis of Bis(indolyl)methanes Front Cover: Pd-Monothiosquaramides: Efficient Catalysts for the Enantioselective Imine Reduction of Dihydro-β-Carbolines (Asian J. Org. Chem. 11/2024) Cover Feature: Diastereoselective Synthesis of Meso-1,2-Diarylethane-1,2-Diamines Via Sodium Reduction of Imidazolines (Asian J. Org. Chem. 11/2024) Front Cover: Direct In Situ Polymer Modification of Titania Nanomaterial Surfaces via UV-irradiated Radical Polymerization (Asian J. Org. Chem. 10/2024) Pd(0)/TPPMS‐Catalyzed Tsuji–Trost Type Cross‐Coupling of Allylic Alcohols with Organoboron Compounds in Water
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1