• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

在KFe(CN)/O体系下通过串联迈克尔加成和氧化反应合成不对称二芳基富马腈

Synthesis of Unsymmetrical Diarylfumaronitriles via Tandem Michael Addition and Oxidation under KFe(CN)/O System.

作者信息

Lu Chongjiu, Ye Min, Long Lipeng, Zheng Yue, Liu Jiameng, Zhang Yue, Chen Zhengwang

机构信息

Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi province, Gannan Normal University, Ganzhou 341000, China.

Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Hunan Normal University, Changsha 410081, China.

出版信息

J Org Chem. 2022 Jan 21;87(2):1545-1553. doi: 10.1021/acs.joc.1c02498. Epub 2022 Jan 11.

DOI:10.1021/acs.joc.1c02498
PMID:35014849
Abstract

An efficient formal alkenyl C-H cyanation reaction has been developed for the general synthesis of unsymmetrical diarylfumaronitriles in good to excellent yields. The reaction was achieved through tandem Michael addition and an oxidative process. The merits of this transformation include the use of KFe(CN) as a safe and nontoxic cyanide source, without an external noble metal catalyst, oxygen-involved reactions, easily available raw materials, good functional group tolerance, high stereoselectivity, and potential further application of the products.

摘要

已经开发出一种高效的正式烯基C-H氰化反应,用于一般合成不对称二芳基富马腈,产率良好至优异。该反应通过串联迈克尔加成和氧化过程实现。这种转化的优点包括使用KFe(CN)作为安全无毒的氰化物源,无需外部贵金属催化剂,涉及氧气的反应,原料容易获得,良好的官能团耐受性,高立体选择性以及产物的潜在进一步应用。

相似文献

1
Synthesis of Unsymmetrical Diarylfumaronitriles via Tandem Michael Addition and Oxidation under KFe(CN)/O System.在KFe(CN)/O体系下通过串联迈克尔加成和氧化反应合成不对称二芳基富马腈
J Org Chem. 2022 Jan 21;87(2):1545-1553. doi: 10.1021/acs.joc.1c02498. Epub 2022 Jan 11.
2
Reductive cyanation of organic chlorides using CO and NH via Triphos-Ni(I) species.使用三膦镍(I)物种通过 CO 和 NH 实现有机氯化物的还原氰化。
Nat Commun. 2020 Aug 14;11(1):4096. doi: 10.1038/s41467-020-17939-2.
3
Cyanide-Free Ce(III)-Catalyzed Highly Efficient Synthesis of α-Iminonitriles from 2-Aminopyridines and Nitroalkenes via Intermolecular Dehydration Reaction.无氰化铈(III)催化2-氨基吡啶与硝基烯烃通过分子间脱水反应高效合成α-亚氨基腈
ACS Omega. 2018 Oct 3;3(10):12520-12529. doi: 10.1021/acsomega.8b02214. eCollection 2018 Oct 31.
4
Cyanation of aryl bromides with K4[Fe(CN)6] catalyzed by dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium, a molecular source of nanoparticles, and the reactions involved in the catalyst-deactivation processes.二氯[双{1-(二环己基膦基)哌啶}]钯催化的 K4[Fe(CN)6]对芳基溴的氰化作用,以及纳米粒子的分子源,以及催化剂失活过程中涉及的反应。
Chemistry. 2012 Mar 5;18(10):2978-86. doi: 10.1002/chem.201102936. Epub 2012 Feb 1.
5
Catalytic cascade synthesis of cyanohydrin esters water/O-induced cyanide transfer from KFe(CN).
Chem Commun (Camb). 2023 Sep 26;59(77):11544-11547. doi: 10.1039/d3cc02743k.
6
Direct cyanation of heteroaromatic compounds mediated by hypervalent iodine(III) reagents: In situ generation of PhI(III)-CN species and their cyano transfer.高价碘(III)试剂介导的杂环芳烃的直接氰化反应:PhI(III)-CN物种的原位生成及其氰基转移
J Org Chem. 2007 Jan 5;72(1):109-16. doi: 10.1021/jo061820i.
7
Aerobic ruthenium-catalyzed oxidative cyanation of tertiary amines with sodium cyanide.钌催化叔胺与氰化钠的有氧氧化氰化反应
J Am Chem Soc. 2003 Dec 17;125(50):15312-3. doi: 10.1021/ja0390303.
8
Oxygenation via C-H/C-C Bond Activation with Molecular Oxygen.利用分子氧通过 C-H/C-C 键活化进行氧合。
Acc Chem Res. 2017 Jul 18;50(7):1640-1653. doi: 10.1021/acs.accounts.7b00108. Epub 2017 Jun 21.
9
Protein control of the formation and decomposition of the CYP119 and CYP101 aryl-iron complexes.细胞色素P450 119和细胞色素P450 101芳基铁配合物形成与分解的蛋白质调控。
J Biol Inorg Chem. 2000 Apr;5(2):204-12. doi: 10.1007/s007750050364.
10
Metal-mediated C-CN Bond Activation in Organic Synthesis.有机合成中金属介导的C-CN键活化
Chem Rev. 2021 Jan 13;121(1):327-344. doi: 10.1021/acs.chemrev.0c00301. Epub 2020 Oct 13.

引用本文的文献

1
Iron(II) Phthalocyanine-Catalyzed Olefination of Aldehydes with Diazoacetonitrile: A Novel Approach to Construct Alkenyl Nitriles.铁(II)酞菁催化醛与重氮乙腈的烯化反应:构建烯基腈的新方法。
ACS Omega. 2024 Jan 9;9(3):3317-3323. doi: 10.1021/acsomega.3c06029. eCollection 2024 Jan 23.
2
Base-promoted highly efficient synthesis of nitrile-substituted cyclopropanes Michael-initiated ring closure.碱促进腈取代环丙烷的高效合成 迈克尔引发的环化反应。
RSC Adv. 2022 Oct 6;12(44):28576-28579. doi: 10.1039/d2ra05393d. eCollection 2022 Oct 4.