• 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

铜卡宾中间体介导的炔烃转化的最新进展。

Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.

机构信息

School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China.

Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.

出版信息

Molecules. 2022 May 11;27(10):3088. doi: 10.3390/molecules27103088.

DOI:10.3390/molecules27103088
PMID:35630567
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9144650/
Abstract

As one of the abundant and inexpensive metals on the earth, copper has demonstrated broad applications in synthetic chemistry and catalysis. Among these copper-catalyzed advances, copper carbenes are versatile and reactive intermediates that can mediate a variety of transformations, which have attracted much attention in the past decades. The present review summarizes two different reaction models that take place between a copper carbene intermediate and alkyne species, including the cross-coupling reaction of copper carbene intermediate with terminal alkyne, and the addition of copper carbene intermediate onto the C-C triple bond. This article will cover the profile from 2010 to 2021 by placing emphasis on the detailed catalytic models and highlighting the synthetic applications offered by these practical and mild methods.

摘要

铜是地球上储量丰富且价格低廉的金属之一,在合成化学和催化领域有着广泛的应用。在这些铜催化的进展中,铜卡宾是多功能且反应性的中间体,可以介导多种转化,这在过去几十年中引起了广泛关注。本综述总结了铜卡宾中间体与炔烃之间发生的两种不同反应模型,包括铜卡宾中间体与末端炔烃的交叉偶联反应,以及铜卡宾中间体加成到 C-C 三键上。本文将重点介绍详细的催化模型,并强调这些实用且温和方法所提供的合成应用,涵盖了 2010 年至 2021 年的研究概况。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/1a6bbb2ab360/molecules-27-03088-sch036.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/feffa6379e2f/molecules-27-03088-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/d9ce7e5c54d4/molecules-27-03088-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/f46f5f5433d4/molecules-27-03088-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/dd37f598bfa0/molecules-27-03088-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/8a1a754f6984/molecules-27-03088-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/f0f16870ae9a/molecules-27-03088-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/88e0a918e37d/molecules-27-03088-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/c7abbcea1a75/molecules-27-03088-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/dcf9887655d5/molecules-27-03088-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/38e929598416/molecules-27-03088-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/5910245357c3/molecules-27-03088-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/fb527275e9c4/molecules-27-03088-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/d4baf308dbc1/molecules-27-03088-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/a4b99b75c226/molecules-27-03088-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/3bd837ac2b6c/molecules-27-03088-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/1d8bdb39c751/molecules-27-03088-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/cdfbc2a9dbc4/molecules-27-03088-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/8072afc121f3/molecules-27-03088-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/b8bcf933aaa9/molecules-27-03088-sch018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/cd840931f7e7/molecules-27-03088-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/8ecf909384c9/molecules-27-03088-sch020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/9b7d1211141c/molecules-27-03088-sch021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/b394d26b2560/molecules-27-03088-sch022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/867e7fe2307f/molecules-27-03088-sch023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/10e5118aaa5e/molecules-27-03088-sch024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/45989ca9b424/molecules-27-03088-sch025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/415ba17df416/molecules-27-03088-sch026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/d58f9e2eb72d/molecules-27-03088-sch027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/2e1694dd3913/molecules-27-03088-sch028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/bac187696b0c/molecules-27-03088-sch029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/2dd125d01437/molecules-27-03088-sch030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/a7fb2c5c7585/molecules-27-03088-sch031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/733ef62f9cdf/molecules-27-03088-sch032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/0a6496294399/molecules-27-03088-sch033.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/708fd724b8aa/molecules-27-03088-sch034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/ef8f0058ad54/molecules-27-03088-sch035.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/1a6bbb2ab360/molecules-27-03088-sch036.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/feffa6379e2f/molecules-27-03088-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/d9ce7e5c54d4/molecules-27-03088-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/f46f5f5433d4/molecules-27-03088-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/dd37f598bfa0/molecules-27-03088-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/8a1a754f6984/molecules-27-03088-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/f0f16870ae9a/molecules-27-03088-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/88e0a918e37d/molecules-27-03088-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/c7abbcea1a75/molecules-27-03088-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/dcf9887655d5/molecules-27-03088-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/38e929598416/molecules-27-03088-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/5910245357c3/molecules-27-03088-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/fb527275e9c4/molecules-27-03088-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/d4baf308dbc1/molecules-27-03088-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/a4b99b75c226/molecules-27-03088-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/3bd837ac2b6c/molecules-27-03088-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/1d8bdb39c751/molecules-27-03088-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/cdfbc2a9dbc4/molecules-27-03088-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/8072afc121f3/molecules-27-03088-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/b8bcf933aaa9/molecules-27-03088-sch018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/cd840931f7e7/molecules-27-03088-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/8ecf909384c9/molecules-27-03088-sch020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/9b7d1211141c/molecules-27-03088-sch021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/b394d26b2560/molecules-27-03088-sch022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/867e7fe2307f/molecules-27-03088-sch023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/10e5118aaa5e/molecules-27-03088-sch024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/45989ca9b424/molecules-27-03088-sch025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/415ba17df416/molecules-27-03088-sch026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/d58f9e2eb72d/molecules-27-03088-sch027.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/2e1694dd3913/molecules-27-03088-sch028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/bac187696b0c/molecules-27-03088-sch029.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/2dd125d01437/molecules-27-03088-sch030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/a7fb2c5c7585/molecules-27-03088-sch031.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/733ef62f9cdf/molecules-27-03088-sch032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/0a6496294399/molecules-27-03088-sch033.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/708fd724b8aa/molecules-27-03088-sch034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/ef8f0058ad54/molecules-27-03088-sch035.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a51/9144650/1a6bbb2ab360/molecules-27-03088-sch036.jpg

相似文献

1
Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.铜卡宾中间体介导的炔烃转化的最新进展。
Molecules. 2022 May 11;27(10):3088. doi: 10.3390/molecules27103088.
2
A non-diazo approach to α-oxo gold carbenes via gold-catalyzed alkyne oxidation.一种通过金催化炔烃氧化制备α-氧代金卡宾的非重氮方法。
Acc Chem Res. 2014 Mar 18;47(3):877-88. doi: 10.1021/ar400181x. Epub 2014 Jan 15.
3
Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes*.环状(烷基)(氨基)卡宾配体实现铜催化末端炔烃的 Markovnikov 硼化和硅化反应:一种多功能构建官能化烯烃的途径*。
Angew Chem Int Ed Engl. 2021 Sep 1;60(36):19871-19878. doi: 10.1002/anie.202106107. Epub 2021 Jul 29.
4
Ruthenium-catalyzed synthesis of functional conjugated dienes via addition of two carbene units to alkynes.钌催化通过向炔烃中添加两个卡宾单元合成功能共轭二烯。
J Am Chem Soc. 2010 Jun 2;132(21):7391-7. doi: 10.1021/ja101064b.
5
Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis.用于多样化氮杂环合成的烯酰胺的过渡金属催化串联反应
Acc Chem Res. 2020 Sep 15;53(9):2003-2019. doi: 10.1021/acs.accounts.0c00417. Epub 2020 Sep 1.
6
Pd-catalyzed cross-coupling of terminal alkynes with ene-yne-ketones: access to conjugated enynes via metal carbene migratory insertion.钯催化末端炔烃与烯炔酮的交叉偶联:通过金属卡宾迁移插入制备共轭烯炔
Chem Commun (Camb). 2015 Jun 30;51(56):11233-5. doi: 10.1039/c5cc03559g.
7
Ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes via a N-sulfonyl-1,2,3-triazole intermediate.通过 N-磺酰基-1,2,3-三唑中间体实现炔丙基环丙烷的环扩张生成高取代的环丁烯。
Chem Commun (Camb). 2013 May 14;49(39):4376-8. doi: 10.1039/c2cc34609e. Epub 2012 Aug 3.
8
Synthesis of isocoumarins through three-component couplings of arynes, terminal alkynes, and carbon dioxide catalyzed by an NHC-copper complex.通过 NHC-铜配合物催化的芳炔、末端炔烃和二氧化碳的三组分偶联反应合成异香豆素。
Angew Chem Int Ed Engl. 2014 Sep 15;53(38):10213-7. doi: 10.1002/anie.201404692. Epub 2014 Jul 23.
9
Copper- and copper-N-heterocyclic carbene-catalyzed C-H activating carboxylation of terminal alkynes with CO2 at ambient conditions.铜和铜杂环卡宾催化的在环境条件下末端炔烃与 CO2 的 C-H 活化羧化反应。
Proc Natl Acad Sci U S A. 2010 Nov 23;107(47):20184-9. doi: 10.1073/pnas.1010962107. Epub 2010 Nov 8.
10
Combining NHC-Cu and Brønsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.结合 NHC-Cu 和 Brønsted 碱催化:手性烯丙基取代/共轭加成与炔基铝试剂和产物的立体特异性异构化为三取代丙二烯。
Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7694-9. doi: 10.1002/anie.201303501. Epub 2013 Jun 18.

引用本文的文献

1
Exploring the capabilities of 2-alkynyl aryl/benzyl azides: synthesis approaches for indoles, quinolines, and their derivatives transition metal catalysis.探索2-炔基芳基/苄基叠氮化物的性能:吲哚、喹啉及其衍生物的合成方法——过渡金属催化
RSC Adv. 2025 Jan 14;15(2):1163-1204. doi: 10.1039/d4ra08280j. eCollection 2025 Jan 9.
2
Tropospheric Fate of Methylhydroxycarbene and the Ability of a Single Water Molecule to Efficiently Promote Its Isomerization into Acetaldehyde.甲基羟基卡宾在对流层中的命运以及单个水分子有效促进其异构化为乙醛的能力。
J Am Chem Soc. 2025 Jan 8;147(1):211-222. doi: 10.1021/jacs.4c08903. Epub 2024 Dec 17.
3

本文引用的文献

1
Copper-Catalyzed Tandem Cross-Coupling and Alkynylogous Aldol Reaction: Access to Chiral Exocyclic α-Allenols.铜催化的串联交叉偶联和炔基同系Aldol 反应:手性外消旋 α-烯醇的合成。
Org Lett. 2021 Jul 2;23(13):5175-5179. doi: 10.1021/acs.orglett.1c01712. Epub 2021 Jun 17.
2
Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides.基于吲哚鎓叶立德重排的催化剂控制区域选择性。
J Am Chem Soc. 2021 Jun 23;143(24):9016-9025. doi: 10.1021/jacs.1c00283. Epub 2021 Jun 14.
3
Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction.
Intramolecular Oxyalkylation of Unactivated Alkenes.
未活化烯烃的分子内氧烷基化反应
Tetrahedron. 2024 Jul 17;161. doi: 10.1016/j.tet.2024.134070. Epub 2024 May 31.
4
Gold-catalyzed carbocyclization and imidization of alkyne-tethered diazo compounds with nitrosoarenes for the synthesis of nitrones and naphthalene derivatives.金催化炔烃键合重氮化合物与亚硝基芳烃的碳环化和酰亚胺化反应合成硝酮和萘衍生物。
Mol Divers. 2023 Oct;27(5):1971-1978. doi: 10.1007/s11030-022-10530-5. Epub 2022 Sep 23.
铜催化末端炔烃的1,1-硼烷基化反应:通过三组分反应制备烯基硼酸酯
Org Lett. 2021 May 7;23(9):3706-3711. doi: 10.1021/acs.orglett.1c01081. Epub 2021 Apr 21.
4
Two Copper-Carbenes from One Diazo Compound.由一个重氮化合物生成的两个铜卡宾。
J Am Chem Soc. 2021 Mar 31;143(12):4837-4843. doi: 10.1021/jacs.1c01483. Epub 2021 Mar 18.
5
Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality.解读烯丙醇的多变化学性质:打破曾经神秘官能团的禁忌
Chem Rev. 2021 Apr 14;121(7):4193-4252. doi: 10.1021/acs.chemrev.0c00986. Epub 2021 Feb 25.
6
Homogeneous Gold-Catalyzed Oxidation Reactions.均相金催化氧化反应。
Chem Rev. 2021 Jul 28;121(14):8979-9038. doi: 10.1021/acs.chemrev.0c00774. Epub 2021 Feb 16.
7
Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C-N, C-C, and C-O Bonds.金属催化的烯丙基化合物的分子间氢官能化反应:通过选择性形成 C-N、C-C 和 C-O 键,轻松获得烯丙基结构。
Chem Rev. 2020 Dec 23;120(24):13545-13598. doi: 10.1021/acs.chemrev.0c00803. Epub 2020 Dec 10.
8
Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes.金催化的特殊活化炔烃、丙二烯和烯烃反应。
Chem Rev. 2021 Jul 28;121(14):8756-8867. doi: 10.1021/acs.chemrev.0c00788. Epub 2020 Nov 23.
9
Isolable Copper(I) η-Cyclopropene Complexes.可分离的一价铜与环丙烯的配合物。
Inorg Chem. 2020 Dec 21;59(24):17860-17865. doi: 10.1021/acs.inorgchem.0c02886. Epub 2020 Nov 8.
10
1,2-Migrations onto Gold Carbene Centers.1,2-迁移至金卡宾中心。
Chem Rev. 2021 Jul 28;121(14):8948-8978. doi: 10.1021/acs.chemrev.0c00811. Epub 2020 Oct 7.