• 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

使用N-羟基邻苯二甲酰亚胺的铜促进的C-O键形成:苄基和烯丙基C-H键的高效选择性官能化

Cu-facilitated C-O bond formation using N-hydroxyphthalimide: efficient and selective functionalization of benzyl and allylic C-H bonds.

作者信息

Lee Ji Min, Park Eun Ju, Cho Seung Hwan, Chang Sukbok

机构信息

Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology, Daejeon 305-701, Republic of Korea.

出版信息

J Am Chem Soc. 2008 Jun 25;130(25):7824-5. doi: 10.1021/ja8031218. Epub 2008 May 31.

DOI:10.1021/ja8031218
PMID:18512912
Abstract

A highly efficient protocol for the benzyl or allylic C-H functionalization of simple hydrocarbons has been developed using stoichiometric amounts of N-hydroxyphthalimide and PhI(OAc)2 in the presence of CuCl catalyst. The reaction was revealed to proceed via a radical pathway, in which phthalimide N-oxyl (PINO) radical plays a dual role, serving as a catalytic hydrogen abstractor from hydrocarbons as well as a stoichiometric reagent to couple with the resultant alkyl radicals.

摘要

在氯化铜催化剂存在下,使用化学计量的N-羟基邻苯二甲酰亚胺和乙酸碘苯(PhI(OAc)₂),已开发出一种用于简单烃类苄基或烯丙基C-H官能化的高效方法。该反应通过自由基途径进行,其中邻苯二甲酰亚胺N-氧基(PINO)自由基起着双重作用,既作为从烃类中夺取氢的催化试剂,又作为与生成的烷基自由基偶联的化学计量试剂。

相似文献

1
Cu-facilitated C-O bond formation using N-hydroxyphthalimide: efficient and selective functionalization of benzyl and allylic C-H bonds.使用N-羟基邻苯二甲酰亚胺的铜促进的C-O键形成:苄基和烯丙基C-H键的高效选择性官能化
J Am Chem Soc. 2008 Jun 25;130(25):7824-5. doi: 10.1021/ja8031218. Epub 2008 May 31.
2
Electron-transfer mechanism in the N-demethylation of N,N-dimethylanilines by the phthalimide-N-oxyl radical.邻苯二甲酰亚胺 -N -氧基自由基使N,N -二甲基苯胺进行N -去甲基化反应中的电子转移机制。
J Org Chem. 2005 Jun 24;70(13):5144-9. doi: 10.1021/jo0503916.
3
Kinetic study of the phthalimide N-oxyl radical in acetic acid. Hydrogen abstraction from substituted toluenes, benzaldehydes, and benzyl alcohols.邻苯二甲酰亚胺氮氧自由基在乙酸中的动力学研究。从取代甲苯、苯甲醛和苄醇中夺取氢原子的反应
J Org Chem. 2003 Nov 28;68(24):9364-70. doi: 10.1021/jo0348017.
4
Mechanisms of reaction of aminoxyl (nitroxide), iminoxyl, and imidoxyl radicals with alkenes and evidence that in the presence of lead tetraacetate, N-hydroxyphthalimide reacts with alkenes by both radical and nonradical mechanisms.氨氧自由基(氮氧化物)、亚胺氧自由基和亚胺基氧自由基与烯烃的反应机制,以及在四乙酸铅存在下,N-羟基邻苯二甲酰亚胺通过自由基和非自由基机制与烯烃反应的证据。
J Org Chem. 2005 Jun 10;70(12):4629-36. doi: 10.1021/jo0504060.
5
Kinetic study of the hydrogen abstraction reaction of the benzotriazole-N-oxyl radical (BTNO) with H-donor substrates.苯并三唑 - N - 氧基自由基(BTNO)与氢供体底物的氢提取反应的动力学研究。
J Org Chem. 2005 Nov 11;70(23):9521-8. doi: 10.1021/jo051615n.
6
Electron-transfer properties of short-lived N-oxyl radicals. Kinetic study of the reactions of benzotriazole-N-oxyl radicals with ferrocenes. Comparison with the phthalimide-N-oxyl radical.短寿命N-氧基自由基的电子转移性质。苯并三唑-N-氧基自由基与二茂铁反应的动力学研究。与邻苯二甲酰亚胺-N-氧基自由基的比较。
J Org Chem. 2009 Aug 7;74(15):5576-83. doi: 10.1021/jo900951c.
7
Hydroxylamines as oxidation catalysts: thermochemical and kinetic studies.羟胺作为氧化催化剂:热化学和动力学研究。
J Org Chem. 2003 Mar 7;68(5):1747-54. doi: 10.1021/jo026660z.
8
Kinetics of self-decomposition and hydrogen atom transfer reactions of substituted phthalimide N-oxyl radicals in acetic acid.取代邻苯二甲酰亚胺氮氧自由基在乙酸中的自分解动力学及氢原子转移反应
J Org Chem. 2005 Jan 7;70(1):238-43. doi: 10.1021/jo048418t.
9
Aerobic Oxidation of 4-Alkyl-N,N-dimethylbenzylamines Catalyzed by N-Hydroxyphthalimide: Protonation-Driven Control over Regioselectivity.N-羟基邻苯二甲酰亚胺催化 4-烷基-N,N-二甲基苄胺的有氧氧化:质子化驱动区域选择性控制。
J Org Chem. 2017 Jun 2;82(11):5761-5768. doi: 10.1021/acs.joc.7b00563. Epub 2017 May 17.
10
Radical amination of C(sp3)-H bonds using N-hydroxyphthalimide and dialkyl azodicarboxylate.使用 N-羟基邻苯二甲酰亚胺和二烷基偶氮二甲酸酯的 C(sp3)-H 键的自由基胺化反应。
J Org Chem. 2012 Nov 16;77(22):9959-69. doi: 10.1021/jo301840e. Epub 2012 Nov 5.

引用本文的文献

1
-Hydroxypiridinedione: A Privileged Heterocycle for Targeting the HBV RNase H.羟啶酮:一种用于靶向 HBV RNase H 的优势杂环。
Molecules. 2024 Jun 20;29(12):2942. doi: 10.3390/molecules29122942.
2
A Horseradish Peroxidase-Mediator System for Benzylic C-H Activation.用于苄基C-H活化的辣根过氧化物酶-介质体系。
ACS Catal. 2022 Oct 7;12(19):12246-12252. doi: 10.1021/acscatal.2c03424. Epub 2022 Sep 26.
3
Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp)-H bonds.碘(III)促进N-羟基邻苯二甲酰亚胺与未活化的C(sp)-H键的交叉脱氢偶联反应。
Commun Chem. 2021 Mar 31;4(1):46. doi: 10.1038/s42004-021-00480-8.
4
Electrochemical PINOylation of Methylarenes: Improving the Scope and Utility of Benzylic Oxidation through Mediated Electrolysis.电化学 PINOylation 甲基芳烃:通过介导的电解改善苄基氧化的范围和实用性。
J Am Chem Soc. 2022 Aug 24;144(33):15295-15302. doi: 10.1021/jacs.2c05974. Epub 2022 Aug 16.
5
Radical C(sp3)-H functionalization and cross-coupling reactions.自由基C(sp3)-H官能团化及交叉偶联反应
Nat Rev Chem. 2022 Jun;6(6):405-427. doi: 10.1038/s41570-022-00388-4. Epub 2022 May 17.
6
Direct C-H amination reactions of arenes with -hydroxyphthalimides catalyzed by cuprous bromide.溴化亚铜催化芳烃与N-羟基邻苯二甲酰亚胺的直接C-H胺化反应。
Beilstein J Org Chem. 2022 Jun 3;18:647-652. doi: 10.3762/bjoc.18.65. eCollection 2022.
7
Benzylic Methylene Functionalizations of Diarylmethanes.苄叉基二芳基甲烷的官能化。
Chem Asian J. 2020 Oct 16;15(20):3135-3161. doi: 10.1002/asia.202000730. Epub 2020 Sep 9.
8
Synthesis of Benzylic Alcohols by C-H Oxidation.通过 C-H 氧化合成苄醇。
J Am Chem Soc. 2019 Nov 13;141(45):17983-17988. doi: 10.1021/jacs.9b09496. Epub 2019 Nov 5.
9
Practical -Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to -Sulfonylimines.实用的——羟基邻苯二甲酰亚胺介导的磺酰胺氧化为磺酰亚胺。
Molecules. 2019 Oct 19;24(20):3771. doi: 10.3390/molecules24203771.
10
Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.光氧化还原/酶协同 C-H 苄位羟化反应。
Angew Chem Int Ed Engl. 2019 Nov 11;58(46):16490-16494. doi: 10.1002/anie.201909426. Epub 2019 Sep 26.