• 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

高价碘诱导的氧化偶联反应(新型无金属偶联反应的进展及其在天然产物合成中的应用)

Hypervalent Iodine-Induced Oxidative Couplings (New Metal-Free Coupling Advances and Their Applications in Natural Product Syntheses).

作者信息

Dohi Toshifumi, Kita Yasuyuki

机构信息

College of Pharmaceutical Science, Ritsumeikan University, 1-1-1 Nojihigasshi, Kusatsu, Shiga, 525-8577, Japan.

Research Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigasshi, Kusatsu, Shiga, 525-8577, Japan.

出版信息

Top Curr Chem. 2016;373:1-23. doi: 10.1007/128_2016_667.

DOI:10.1007/128_2016_667
PMID:26920160
Abstract

Recently, hypervalent iodine reagents have been extensively used in organic synthesis. A variety of reactions available for natural product syntheses have been developed using phenyliodine(III) diacetate (PIDA), phenyliodine(III) bis(trifluoroacetate) (PIFA), and other iodine(III) and (V) reagents. These reactions are expected to have applications in pharmaceutical and agrochemical processes because of their safety, mild reaction conditions, and high yields of pure products. Under such considerations, this chapter focuses on the oxidative coupling reactions of hypervalent iodine reagents found in total syntheses of biologically active natural products and their related compounds.

摘要

近年来,高价碘试剂已在有机合成中得到广泛应用。利用二醋酸碘苯(PIDA)、双(三氟乙酸)碘苯(PIFA)以及其他碘(III)和碘(V)试剂,已开发出多种可用于天然产物合成的反应。由于这些反应具有安全性、温和的反应条件以及高纯度产物收率,有望在制药和农用化学品工艺中得到应用。基于这些考虑,本章重点介绍在生物活性天然产物及其相关化合物的全合成中发现的高价碘试剂的氧化偶联反应。

相似文献

1
Hypervalent Iodine-Induced Oxidative Couplings (New Metal-Free Coupling Advances and Their Applications in Natural Product Syntheses).高价碘诱导的氧化偶联反应(新型无金属偶联反应的进展及其在天然产物合成中的应用)
Top Curr Chem. 2016;373:1-23. doi: 10.1007/128_2016_667.
2
Pioneering Metal-Free Oxidative Coupling Strategy of Aromatic Compounds Using Hypervalent Iodine Reagents.使用高价碘试剂实现芳香族化合物的无金属氧化偶联的开拓性策略。
Chem Rec. 2015 Oct;15(5):886-906. doi: 10.1002/tcr.201500020. Epub 2015 Jul 29.
3
[Development of intramolecular oxidative phenolic coupling reactions using hypervalent iodine (III) reagents and their application to the synthesis of Amaryllidaceae alkaloids].[使用高价碘(III)试剂的分子内氧化酚偶联反应的发展及其在石蒜科生物碱合成中的应用]
Yakugaku Zasshi. 2000 Oct;120(10):1061-73. doi: 10.1248/yakushi1947.120.10_1061.
4
Convenient Synthesis of 6,7,12,13-Tetrahydro-5-Cyclohepta[2,1-:3,4-]diindole Derivatives Mediated by Hypervalent Iodine (III) Reagent.高碘(III)试剂介导的 6,7,12,13-四氢-5-环庚[2,1-:3,4-]二吲哚衍生物的便捷合成。
Molecules. 2019 Mar 8;24(5):960. doi: 10.3390/molecules24050960.
5
[Development of novel oxidation reactions using hypervalent iodine reagents and their application to total synthesis of biologically active natural products].[使用高价碘试剂开发新型氧化反应及其在生物活性天然产物全合成中的应用]
Yakugaku Zasshi. 2000 Jul;120(7):620-9. doi: 10.1248/yakushi1947.120.7_620.
6
A new synthesis of dienone lactones using a combination of hypervalent iodine(III) reagent and heteropoly acid.使用高价碘(III)试剂和杂多酸组合的二烯酮内酯新合成方法。
Chem Commun (Camb). 2005 May 21(19):2465-7. doi: 10.1039/b501792k. Epub 2005 Mar 24.
7
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.
8
Metal-free iodine(III)-promoted synthesis of isoquinolones.无金属碘(III)促进的异喹啉酮合成。
J Org Chem. 2014 Nov 21;79(22):10988-98. doi: 10.1021/jo5020307. Epub 2014 Nov 10.
9
Glycosylation Reaction of Thioglycosides by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter.以高价碘(III)试剂作为优良促进剂的硫代糖苷糖基化反应
Chem Pharm Bull (Tokyo). 2016;64(7):838-44. doi: 10.1248/cpb.c16-00203.
10
Recycling and catalytic approaches for the development of a rare-metal-free synthetic method using hypervalent iodine reagent.利用高价碘试剂开发无稀有金属合成方法的循环利用和催化方法。
Chem Pharm Bull (Tokyo). 2010 Feb;58(2):135-42. doi: 10.1248/cpb.58.135.

引用本文的文献

1
Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.碘代芳烃的活化:向绿色可持续转化迈进一大步。
Chem Rev. 2025 Mar 26;125(6):3440-3550. doi: 10.1021/acs.chemrev.4c00808. Epub 2025 Mar 7.
2
Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.高价碘(III)试剂在合成应用中的最新进展
Chem Rev. 2024 Oct 9;124(19):11108-11186. doi: 10.1021/acs.chemrev.4c00303. Epub 2024 Sep 13.
3
Oxidative Cyclization at -Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine.
酚的 - 位的氧化环化:3-(苯乙胺基)去甲氧基(氧)阿朴啡的改进全合成。
Mar Drugs. 2023 May 19;21(5):311. doi: 10.3390/md21050311.
4
"Cut and Paste" Processes in the Search of Bioactive Products: One-Pot, Metal-free -Radical Scission-Oxidation-Addition of , or -Nucleophiles.寻找生物活性产品中的“剪切与粘贴”过程:一锅法、无金属的、、或亲核试剂的自由基断裂-氧化-加成反应
Front Chem. 2022 May 18;10:884124. doi: 10.3389/fchem.2022.884124. eCollection 2022.
5
Iminoxyl radicals -butylperoxyl radical in competitive oxidative C-O coupling with β-dicarbonyl compounds. Oxime ether formation prevails over Kharasch peroxidation.亚胺氧基自由基——丁基过氧自由基与β -二羰基化合物发生竞争性氧化C - O偶联反应。肟醚的形成优先于卡拉施过氧化反应。
RSC Adv. 2018 Feb 5;8(11):5670-5677. doi: 10.1039/c7ra13587d. eCollection 2018 Feb 2.
6
Recent discoveries on the structure of iodine(iii) reagents and their use in cross-nucleophile coupling.碘(III)试剂的结构及其在交叉亲核偶联中的应用的最新发现。
Chem Sci. 2021 Jan 7;12(3):853-864. doi: 10.1039/d0sc03266b.
7
The mechanochemical synthesis of quinazolin-4(3)-ones by controlling the reactivity of IBX.通过控制IBX的反应活性实现喹唑啉-4(3)-酮的机械化学合成
Beilstein J Org Chem. 2018 Sep 12;14:2396-2403. doi: 10.3762/bjoc.14.216. eCollection 2018.
8
Selective carboxylation of reactive benzylic C-H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system.通过高价碘(III)/无机溴化物氧化体系实现活性苄基C-H键的选择性羧化反应。
Beilstein J Org Chem. 2018 May 16;14:1087-1094. doi: 10.3762/bjoc.14.94. eCollection 2018.