• 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

钯催化叠氮化物与异腈的交叉偶联反应。

Palladium-catalyzed cross-coupling reaction of azides with isocyanides.

作者信息

Zhang Zhen, Li Zongyang, Fu Bin, Zhang Zhenhua

机构信息

Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, People's Repubic of China.

出版信息

Chem Commun (Camb). 2015 Nov 25;51(91):16312-5. doi: 10.1039/c5cc05981j.

DOI:10.1039/c5cc05981j
PMID:26419341
Abstract

An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.

摘要

开发了一种高效的钯催化叠氮化物与异腈的交叉偶联反应,为合成不对称碳二亚胺提供了一条通用的合成路线,产率优异。该方法具有广泛的底物范围,不仅包括芳基叠氮化物,还包括未活化的苄基和烷基叠氮化物。此外,以一锅法实现了从易得的底物出发,通过钯催化的偶联与串联胺插入级联反应来获得不对称三取代胍。

相似文献

1
Palladium-catalyzed cross-coupling reaction of azides with isocyanides.钯催化叠氮化物与异腈的交叉偶联反应。
Chem Commun (Camb). 2015 Nov 25;51(91):16312-5. doi: 10.1039/c5cc05981j.
2
Triazole-based monophosphine ligands for palladium-catalyzed cross-coupling reactions of aryl chlorides.用于钯催化芳基氯交叉偶联反应的基于三唑的单膦配体
J Org Chem. 2006 May 12;71(10):3928-34. doi: 10.1021/jo060321e.
3
Sequential Pd(0)/Fe(III) Catalyzed Azide-Isocyanide Coupling/Cyclization Reaction: One-Pot Synthesis of Aminotetrazoles.连续钯(0)/铁(III)催化的叠氮化物-异腈偶联/环化反应:氨基四唑的一锅法合成
J Org Chem. 2018 Aug 17;83(16):9530-9537. doi: 10.1021/acs.joc.8b01261. Epub 2018 Aug 6.
4
Rhodium-Catalyzed Tandem Reaction of Isocyanides with Azides and Oxygen Nucleophiles: Synthesis of Isoureas.铑催化异腈与叠氮化物和氧亲核试剂的串联反应:异脲的合成
J Org Chem. 2019 Jan 4;84(1):53-59. doi: 10.1021/acs.joc.8b01842. Epub 2018 Dec 19.
5
Synthesis of carbodiimides by I2/CHP-mediated cross-coupling reaction of isocyanides with amines under metal-free conditions.在无金属条件下,通过 I2/CHP 介导的异氰化物与胺的交叉偶联反应合成碳二亚胺。
Org Lett. 2015 Apr 17;17(8):1974-7. doi: 10.1021/acs.orglett.5b00722. Epub 2015 Mar 31.
6
Unmasked acyl anion equivalent from acid chloride with indium: reversed-polarity synthesis of unsymmetric aryl aryl and alkenyl aryl ketone through palladium-catalyzed cross-coupling reaction.酰氯脱掩的三价铟试剂:通过钯催化交叉偶联反应实现不对称芳基芳基和烯基芳基酮的反极性合成。
Org Lett. 2014 Feb 21;16(4):1144-7. doi: 10.1021/ol500003g. Epub 2014 Feb 7.
7
Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles.铜/钯催化的叠氮化物、炔烃和芳基卤化物的三组分点击反应:三取代三唑的一锅法合成策略
Org Lett. 2015 Jun 5;17(11):2860-3. doi: 10.1021/acs.orglett.5b01342. Epub 2015 May 22.
8
Palladium-catalyzed intermolecular aerobic oxidative cyclization of 2-ethynylanilines with isocyanides: regioselective synthesis of 4-halo-2-aminoquinolines.钯催化 2-炔基苯胺与异氰的分子间有氧氧化环化反应:4-卤代-2-氨基喹啉的区域选择性合成。
J Org Chem. 2013 Oct 18;78(20):10319-28. doi: 10.1021/jo401707j. Epub 2013 Oct 8.
9
Palladium-catalyzed/norbornene-mediated C-H activation/N-tosylhydrazone insertion reaction: a route to highly functionalized vinylarenes.钯催化/降冰片烯介导的C-H活化/N-对甲苯磺酰腙插入反应:一条通往高度官能化乙烯基芳烃的途径。
Chemistry. 2014 May 26;20(22):6745-51. doi: 10.1002/chem.201402097. Epub 2014 Apr 25.
10
Rhodium-catalyzed direct C-H amination of benzamides with aryl azides: a synthetic route to diarylamines.铑催化的苯甲酰胺与芳基叠氮化物的直接 C-H 胺化反应:二芳基胺的合成途径。
Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9904-8. doi: 10.1002/anie.201205723. Epub 2012 Aug 31.

引用本文的文献

1
Nitrene-transfer from azides to isocyanides: Unveiling its versatility as a promising building block for the synthesis of bioactive heterocycles.叠氮化物向异腈的氮烯转移:揭示其作为合成生物活性杂环的有前景构件的多功能性。
iScience. 2024 Feb 23;27(4):109311. doi: 10.1016/j.isci.2024.109311. eCollection 2024 Apr 19.
2
Unanticipated switch of reactivity of isonitrile via N≡C bond scission: Cascade formation of symmetrical sulfonyl guanidine.异腈通过N≡C键断裂发生意外的反应性转变:对称磺酰胍的级联形成。
iScience. 2023 Jul 3;26(8):107258. doi: 10.1016/j.isci.2023.107258. eCollection 2023 Aug 18.
3
Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide-Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety.
通过碳二亚胺利用叠氮化物-异氰化物交叉偶联反应,以源自吩噻嗪部分的中离子单重态钯卡宾配合物为催化剂,合成杂环苯并恶唑和苯并咪唑骨架。
ACS Omega. 2023 Mar 14;8(12):11039-11064. doi: 10.1021/acsomega.2c07875. eCollection 2023 Mar 28.
4
Transition metal-catalysed carbene- and nitrene transfer to carbon monoxide and isocyanides.过渡金属催化的卡宾和氮烯向一氧化碳和异氰化物的转移。
Chem Soc Rev. 2022 Jul 18;51(14):5842-5877. doi: 10.1039/d1cs00305d.
5
Access to 1-amino-3,4-dihydroisoquinolines palladium-catalyzed C-H bond aminoimidoylation reaction from functionalized isocyanides.从官能化异腈出发通过钯催化的C-H键氨基亚胺基化反应制备1-氨基-3,4-二氢异喹啉
RSC Adv. 2019 Dec 18;9(72):42072-42076. doi: 10.1039/c9ra09139d.
6
Carbodiimide Synthesis via Ti-Catalyzed Nitrene Transfer from Diazenes to Isocyanides.通过钛催化二氮烯向异腈的氮烯转移合成碳二亚胺。
ACS Catal. 2019 Dec 6;9(12):11753-11762. doi: 10.1021/acscatal.9b04107. Epub 2019 Nov 11.