• 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

铜催化三氟甲基化反应的进展

Progress in copper-catalyzed trifluoromethylation.

作者信息

Li Guan-Bao, Zhang Chao, Song Chun, Ma Yu-Dao

机构信息

School of Pharmaceutical sciences, Shandong University, 44 West Culture Road, Jinan 250012, PR China.

Department of chemistry, Shandong University, 27 Shanda South Road, Jinan 250100, PR China.

出版信息

Beilstein J Org Chem. 2018 Jan 17;14:155-181. doi: 10.3762/bjoc.14.11. eCollection 2018.

DOI:10.3762/bjoc.14.11
PMID:29441139
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5789444/
Abstract

The introduction of trifluoromethyl groups into organic molecules has attracted great attention in the past five years. In this review, we describe the recent efforts in the development of trifluoromethylation via copper catalysis using nucleophilic, electrophilic or radical trifluoromethylation reagents.

摘要

在过去五年中,将三氟甲基引入有机分子已引起了极大关注。在本综述中,我们描述了近期使用亲核、亲电或自由基三氟甲基化试剂通过铜催化进行三氟甲基化反应开发方面所做的努力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/57e5291e861a/Beilstein_J_Org_Chem-14-155-g034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/a95a419818c0/Beilstein_J_Org_Chem-14-155-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/ea4269ab8ab6/Beilstein_J_Org_Chem-14-155-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/edaafdb307d5/Beilstein_J_Org_Chem-14-155-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/14854f16a6eb/Beilstein_J_Org_Chem-14-155-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/105ec41d0062/Beilstein_J_Org_Chem-14-155-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/1560ccd81bc8/Beilstein_J_Org_Chem-14-155-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/71b6388ae064/Beilstein_J_Org_Chem-14-155-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/0e4ccc60c675/Beilstein_J_Org_Chem-14-155-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/55848275c7a3/Beilstein_J_Org_Chem-14-155-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/d8cb42aa9efc/Beilstein_J_Org_Chem-14-155-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/554b0529c229/Beilstein_J_Org_Chem-14-155-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/70f0239fe973/Beilstein_J_Org_Chem-14-155-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/13cb3a51dd03/Beilstein_J_Org_Chem-14-155-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/4ddf0b64c426/Beilstein_J_Org_Chem-14-155-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/bec901711f9d/Beilstein_J_Org_Chem-14-155-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/7abddf52d208/Beilstein_J_Org_Chem-14-155-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/c79e3b9c86b7/Beilstein_J_Org_Chem-14-155-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/f05961f80ffb/Beilstein_J_Org_Chem-14-155-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/80472d3b7609/Beilstein_J_Org_Chem-14-155-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/93d751ed9e16/Beilstein_J_Org_Chem-14-155-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/e139590d7f03/Beilstein_J_Org_Chem-14-155-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/94a98ca1002e/Beilstein_J_Org_Chem-14-155-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/24ef0437bbeb/Beilstein_J_Org_Chem-14-155-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/590e2ff2ec7d/Beilstein_J_Org_Chem-14-155-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/ae3e6f8ef3fb/Beilstein_J_Org_Chem-14-155-g026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/f17a177b5438/Beilstein_J_Org_Chem-14-155-g028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/9668a17db8f2/Beilstein_J_Org_Chem-14-155-g030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/abeb3ca85e90/Beilstein_J_Org_Chem-14-155-g032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/57e5291e861a/Beilstein_J_Org_Chem-14-155-g034.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/a95a419818c0/Beilstein_J_Org_Chem-14-155-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/ea4269ab8ab6/Beilstein_J_Org_Chem-14-155-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/edaafdb307d5/Beilstein_J_Org_Chem-14-155-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/14854f16a6eb/Beilstein_J_Org_Chem-14-155-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/105ec41d0062/Beilstein_J_Org_Chem-14-155-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/1560ccd81bc8/Beilstein_J_Org_Chem-14-155-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/71b6388ae064/Beilstein_J_Org_Chem-14-155-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/0e4ccc60c675/Beilstein_J_Org_Chem-14-155-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/55848275c7a3/Beilstein_J_Org_Chem-14-155-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/d8cb42aa9efc/Beilstein_J_Org_Chem-14-155-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/554b0529c229/Beilstein_J_Org_Chem-14-155-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/70f0239fe973/Beilstein_J_Org_Chem-14-155-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/13cb3a51dd03/Beilstein_J_Org_Chem-14-155-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/4ddf0b64c426/Beilstein_J_Org_Chem-14-155-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/bec901711f9d/Beilstein_J_Org_Chem-14-155-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/7abddf52d208/Beilstein_J_Org_Chem-14-155-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/c79e3b9c86b7/Beilstein_J_Org_Chem-14-155-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/f05961f80ffb/Beilstein_J_Org_Chem-14-155-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/80472d3b7609/Beilstein_J_Org_Chem-14-155-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/93d751ed9e16/Beilstein_J_Org_Chem-14-155-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/e139590d7f03/Beilstein_J_Org_Chem-14-155-g022.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/94a98ca1002e/Beilstein_J_Org_Chem-14-155-g023.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/24ef0437bbeb/Beilstein_J_Org_Chem-14-155-g024.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/590e2ff2ec7d/Beilstein_J_Org_Chem-14-155-g025.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/ae3e6f8ef3fb/Beilstein_J_Org_Chem-14-155-g026.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/f17a177b5438/Beilstein_J_Org_Chem-14-155-g028.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/9668a17db8f2/Beilstein_J_Org_Chem-14-155-g030.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/abeb3ca85e90/Beilstein_J_Org_Chem-14-155-g032.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f950/5789444/57e5291e861a/Beilstein_J_Org_Chem-14-155-g034.jpg

相似文献

1
Progress in copper-catalyzed trifluoromethylation.铜催化三氟甲基化反应的进展
Beilstein J Org Chem. 2018 Jan 17;14:155-181. doi: 10.3762/bjoc.14.11. eCollection 2018.
2
Oxidative trifluoromethylation and trifluoromethylthiolation reactions using (trifluoromethyl)trimethylsilane as a nucleophilic CF3 source.使用(三氟甲基)三甲基硅烷作为亲核 CF3 源的氧化三氟甲基化和三氟甲硫基化反应。
Acc Chem Res. 2014 May 20;47(5):1513-22. doi: 10.1021/ar4003202. Epub 2014 Apr 28.
3
Recent advances in trifluoromethylation of organic compounds using Umemoto's reagents.使用梅本试剂对有机化合物进行三氟甲基化的最新进展。
Org Biomol Chem. 2014 Sep 14;12(34):6580-9. doi: 10.1039/c4ob00671b.
4
Current State of Microflow Trifluoromethylation Reactions.微流三氟甲基化反应的现状
Chem Rec. 2023 Sep;23(9):e202300117. doi: 10.1002/tcr.202300117. Epub 2023 Jun 12.
5
Recent progress in asymmetric fluorination and trifluoromethylation reactions.近年来不对称氟化和三氟甲基化反应的研究进展。
Curr Top Med Chem. 2014;14(7):901-40. doi: 10.2174/1568026614666140202205531.
6
Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.配体控制的区域选择性铜催化三氟甲基化反应以生成(三氟甲基)丙二烯
Org Lett. 2015 May 15;17(10):2506-9. doi: 10.1021/acs.orglett.5b01027. Epub 2015 Apr 24.
7
Copper-Catalyzed Trifluoromethylation of Alkoxypyridine Derivatives.铜催化烷氧基吡啶衍生物的三氟甲基化反应。
Molecules. 2020 Oct 16;25(20):4766. doi: 10.3390/molecules25204766.
8
Copper-catalyzed nucleophilic trifluoromethylation of allylic halides: a simple approach to allylic trifluoromethylation.铜催化烯丙基卤化物的亲核三氟甲基化反应:一种实现烯丙基三氟甲基化的简便方法。
Chemistry. 2012 Oct 15;18(42):13255-8. doi: 10.1002/chem.201202853. Epub 2012 Sep 10.
9
Electrophilic trifluoromethylation of carbonyl compounds and their nitrogen derivatives under copper catalysis.铜催化下羰基化合物及其氮衍生物的亲电三氟甲基化反应。
Chem Commun (Camb). 2016 Jan 18;52(5):869-81. doi: 10.1039/c5cc05954b.
10
Recent advances in trifluoromethylation reactions with electrophilic trifluoromethylating reagents.亲电三氟甲基化试剂参与的三氟甲基化反应的最新进展。
Chemistry. 2014 Dec 15;20(51):16806-29. doi: 10.1002/chem.201404005. Epub 2014 Oct 21.

引用本文的文献

1
Fluorinating the Sugar and the Nucleotide: Exploring Fluorination Within GDP-Mannose Probes Using Chemoenzymatic Synthesis.对糖和核苷酸进行氟化:利用化学酶法合成探索GDP-甘露糖探针中的氟化作用。
JACS Au. 2025 Jul 31;5(8):3994-4001. doi: 10.1021/jacsau.5c00626. eCollection 2025 Aug 25.
2
Copper-Mediated -CF(OCF)(CFH) Transfer to Organic Electrophiles.铜介导的 -CF(OCF)(CFH) 转移至有机亲电试剂
ACS Org Inorg Au. 2024 Sep 20;4(6):628-639. doi: 10.1021/acsorginorgau.4c00038. eCollection 2024 Dec 4.
3
The Role of Electron Transfer in Copper-Mediated C(sp)-H Trifluoromethylation.

本文引用的文献

1
Highly mono-selective ortho-trifluoromethylation of benzamides via 8-aminoquinoline assisted Cu-promoted C-H activations.通过8-氨基喹啉辅助的铜促进C-H活化实现苯甲酰胺的高度单选择性邻三氟甲基化反应。
Chem Commun (Camb). 2016 May 21;52(41):6845-8. doi: 10.1039/c6cc02412b. Epub 2016 May 6.
2
Cu-Catalyzed C-H Trifluoromethylation of 3-Arylprop-1-ynes for the Selective Construction of Allenic Csp(2)-CF3 and Propargyl Csp(3)-CF3 Bonds.用于选择性构建联烯型Csp(2)-CF3键和炔丙基型Csp(3)-CF3键的3-芳基丙-1-炔的铜催化C-H三氟甲基化反应
Org Lett. 2016 Mar 4;18(5):1000-3. doi: 10.1021/acs.orglett.6b00120. Epub 2016 Feb 17.
3
电子转移在铜介导的C(sp)-H三氟甲基化反应中的作用
Angew Chem Int Ed Engl. 2025 Feb 24;64(9):e202420677. doi: 10.1002/anie.202420677. Epub 2024 Dec 12.
4
Electrochemical trifluoromethylation of alkynes: the unique role of DMSO as a masking auxiliary.炔烃的电化学三氟甲基化反应:二甲基亚砜作为掩蔽助剂的独特作用
Chem Sci. 2024 Nov 4;15(47):19739-19744. doi: 10.1039/d4sc06780k. eCollection 2024 Dec 4.
5
Deoxytrifluoromethylation/aromatization of cyclohexan(en)ones to access highly substituted trifluoromethyl arenes.环己烯酮的脱氧三氟甲基化/芳构化反应以制备高度取代的三氟甲基芳烃。
Nat Commun. 2024 Sep 9;15(1):7882. doi: 10.1038/s41467-024-52035-9.
6
Development of Benziodarone Analogues with Enhanced Potency for Selective Binding to Transthyretin in Human Plasma.具有增强效力的苯碘达隆类似物的开发,用于在人血浆中选择性结合转甲状腺素蛋白。
J Med Chem. 2024 Apr 26;67(9):6987-7005. doi: 10.1021/acs.jmedchem.3c02286.
7
Copper-Mediated N-Trifluoromethylation of O-Benzoylhydroxylamines.铜介导的O-苯甲酰基羟胺的N-三氟甲基化反应
Chemistry. 2024 Jan 26;30(6):e202303314. doi: 10.1002/chem.202303314. Epub 2023 Dec 7.
8
Thiophenium Salts as New Oxidant for Redox Polymerization under Mild- and Low-Toxicity Conditions.噻吩鎓盐在温和低毒条件下用于氧化还原聚合的新型氧化剂。
Molecules. 2023 Jan 7;28(2):627. doi: 10.3390/molecules28020627.
9
Broad-scope Syntheses of [ C/ F]Trifluoromethylarenes from Aryl(mesityl)iodonium Salts.芳基(均三甲苯基)碘𬭩盐的[C/F]三氟甲基芳烃的宽范围合成。
Chemistry. 2023 Apr 25;29(24):e202204004. doi: 10.1002/chem.202204004. Epub 2023 Mar 20.
10
Advances in [F]Trifluoromethylation Chemistry for PET Imaging.氟[F]三氟甲基化反应在正电子发射断层成像(PET)中的应用进展。
Molecules. 2021 Oct 27;26(21):6478. doi: 10.3390/molecules26216478.
Decarboxylative Trifluoromethylating Reagent [Cu(O CCF )(phen)] and Difluorocarbene Precursor [Cu(phen) ][O CCF Cl].
脱羧三氟甲基化试剂[Cu(OCF)(phen)]和二氟卡宾前体[Cu(phen)][OCFCl]
Chemistry. 2016 Feb;22(6):2075-2084. doi: 10.1002/chem.201504306. Epub 2016 Jan 12.
4
Benzylic C-H trifluoromethylation of phenol derivatives.苯酚衍生物的苄基C-H三氟甲基化反应。
Chem Commun (Camb). 2015 Dec 4;51(93):16675-8. doi: 10.1039/c5cc07011b. Epub 2015 Oct 2.
5
Copper-Promoted Trifluoromethanesulfonylation and Trifluoromethylation of Arenediazonium Tetrafluoroborates with NaSO2CF3.铜促进四氟硼酸重氮苯与三氟甲亚磺酸钠的三氟甲磺酰化和三氟甲基化反应
J Org Chem. 2015 Aug 7;80(15):7658-65. doi: 10.1021/acs.joc.5b01295. Epub 2015 Jul 24.
6
Trifluoromethyl-substituted sulfonium ylide: Rh-catalyzed carbenoid addition to trifluoromethylthioether.三氟甲基取代的硫叶立德:铑催化的类卡宾对三氟甲硫醚的加成反应。
Org Lett. 2015 Jun 5;17(11):2752-5. doi: 10.1021/acs.orglett.5b01170. Epub 2015 May 14.
7
Catalytic trifluoromethylation of aryl- and vinylboronic acids by 2-cyclopropyl-1-(trifluoromethyl)benzo[b]thiophenium triflate.三氟甲磺酸2-环丙基-1-(三氟甲基)苯并[b]噻吩鎓催化芳基硼酸和乙烯基硼酸的三氟甲基化反应
Org Lett. 2015 Apr 3;17(7):1632-5. doi: 10.1021/acs.orglett.5b00164. Epub 2015 Mar 18.
8
Recent developments in the trifluoromethylation of alkynes.炔烃三氟甲基化反应的最新进展
Chemistry. 2015 May 18;21(21):7648-61. doi: 10.1002/chem.201406432. Epub 2015 Mar 3.
9
Carbon trifluoromethylation reactions of hydrocarbon derivatives and heteroarenes.烃类衍生物和杂芳烃的三氟甲基化反应。
Chem Rev. 2015 Feb 25;115(4):1847-935. doi: 10.1021/cr500368h. Epub 2015 Jan 30.
10
Exceedingly fast copper(II)-promoted ortho C-H trifluoromethylation of arenes using TMSCF₃.使用 TMSCF₃ 实现的铜(II)促进的芳基邻位 C-H 三氟甲基化反应,具有极快的反应速率。
Angew Chem Int Ed Engl. 2014 Sep 22;53(39):10439-42. doi: 10.1002/anie.201404822. Epub 2014 Aug 5.