• 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

铜催化碘代芳烃与三氟甲基金属试剂的三氟甲基化反应。

Copper-catalyzed trifluoromethylation of aryl iodides with potassium (trifluoromethyl)trimethoxyborate.

机构信息

Fachbereich Organische Chemie, TU-Kaiserslautern, Kaiserslautern, Germany.

出版信息

Chemistry. 2011 Feb 25;17(9):2689-97. doi: 10.1002/chem.201002749. Epub 2011 Jan 27.

DOI:10.1002/chem.201002749
PMID:21274956
Abstract

Potassium (trifluoromethyl)trimethoxyborate is introduced as a new source of CF(3) nucleophiles in copper-catalyzed trifluoromethylation reactions. The crystalline salt is stable on storage, easy to handle, and can be obtained in near-quantitative yields simply by mixing B(OMe)(3), CF(3)SiMe(3), and KF. The trifluoromethylation reagent allows the conversion of various aryl iodides into the corresponding benzotrifluorides in high yields under mild, base-free conditions in the presence of catalytic quantities of a Cu(I)/1,10-phenanthroline complex.

摘要

三氟甲基三氟甲氧基硼酸钾被引入到铜催化的三氟甲基化反应中,作为一种新的 CF3 亲核试剂来源。这种晶体盐在储存时稳定,易于处理,只需将 B(OMe)3、CF3SiMe3 和 KF 混合即可近乎定量地获得。在催化量的 Cu(I)/1,10-菲咯啉配合物存在下,该三氟甲基化试剂在温和、无碱条件下,可将各种芳基碘转化为相应的苯并三氟化物,产率很高。

相似文献

1
Copper-catalyzed trifluoromethylation of aryl iodides with potassium (trifluoromethyl)trimethoxyborate.铜催化碘代芳烃与三氟甲基金属试剂的三氟甲基化反应。
Chemistry. 2011 Feb 25;17(9):2689-97. doi: 10.1002/chem.201002749. Epub 2011 Jan 27.
2
Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide.铜催化碘代芳烃与三氟甲基锌试剂的三氟甲基化反应,三氟甲基锌试剂由三氟碘甲烷原位制备得到。
Beilstein J Org Chem. 2013 Nov 8;9:2404-9. doi: 10.3762/bjoc.9.277. eCollection 2013.
3
Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes.铜催化的杂芳烃直接 C-H 氧化三氟甲基化反应。
J Am Chem Soc. 2012 Jan 18;134(2):1298-304. doi: 10.1021/ja209992w. Epub 2011 Dec 21.
4
Aromatic trifluoromethylation catalytic in copper.铜催化的芳香族三氟甲基化反应
Chem Commun (Camb). 2009 Apr 14(14):1909-11. doi: 10.1039/b823249k. Epub 2009 Feb 23.
5
Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides.温和且高效的铜催化芳基碘化物和溴化物的氰化反应。
Chemistry. 2005 Apr 8;11(8):2483-92. doi: 10.1002/chem.200400979.
6
Stable but reactive perfluoroalkylzinc reagents: application in ligand-free copper-catalyzed perfluoroalkylation of aryl iodides.稳定但具反应活性的全氟烷基锌试剂:在无配体铜催化芳基碘的全氟烷基化反应中的应用
Chemistry. 2015 Jan 2;21(1):96-100. doi: 10.1002/chem.201405677. Epub 2014 Nov 13.
7
Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides.高效且温和的铜催化芳基溴化物和碘化物的N-芳基化和C-芳基化反应
Chemistry. 2004 Nov 5;10(22):5607-22. doi: 10.1002/chem.200400582.
8
Aryl triolborates: novel reagent for copper-catalyzed N arylation of amines, anilines, and imidazoles.芳基三醇硼酸酯:用于铜催化胺、苯胺和咪唑的N-芳基化的新型试剂。
Chem Asian J. 2008 Sep 1;3(8-9):1517-22. doi: 10.1002/asia.200800135.
9
CF3 oxonium salts, O-(trifluoromethyl)dibenzofuranium salts: in situ synthesis, properties, and application as a real CF3+ species reagent.三氟甲氧基鎓盐、O-(三氟甲基)二苯并呋喃鎓盐:原位合成、性质及作为真正的CF3+物种试剂的应用。
J Org Chem. 2007 Aug 31;72(18):6905-17. doi: 10.1021/jo070896r. Epub 2007 Aug 4.
10
Oxidative trifluoromethylation of arylboronates with shelf-stable potassium (trifluoromethyl)trimethoxyborate.芳基硼酸酯与稳定的三氟甲基三甲氧基硼酸钾的氧化三氟甲基化反应。
Chemistry. 2012 Feb 6;18(6):1577-81. doi: 10.1002/chem.201102652. Epub 2012 Jan 11.

引用本文的文献

1
Uncovering a CF Effect on X-ray Absorption Energies of [Cu(CF ) ] and Related Copper Compounds by Using Resonant Diffraction Anomalous Fine Structure (DAFS) Measurements.通过使用共振衍射反常精细结构(DAFS)测量揭示CF对[Cu(CF ) ]及相关铜化合物X射线吸收能量的影响。
Angew Chem Int Ed Engl. 2023 Dec 18;62(51):e202313744. doi: 10.1002/anie.202313744. Epub 2023 Nov 20.
2
Localized nuclear reaction breaks boron drug capsules loaded with immune adjuvants for cancer immunotherapy.局部核反应打破了装载免疫佐剂的硼药物胶囊,用于癌症免疫治疗。
Nat Commun. 2023 Apr 5;14(1):1884. doi: 10.1038/s41467-023-37253-x.
3
Application of Vinamidinium Salt Chemistry for a Palladium Free Synthesis of Anti-Malarial MMV048: A "Bottom-Up" Approach.
用于无钯合成抗疟药 MMV048 的戊脒盐化学应用:一种“自下而上”的方法。
Org Lett. 2021 Jul 16;23(14):5400-5404. doi: 10.1021/acs.orglett.1c01725. Epub 2021 Jun 29.
4
Metallaphotoredox Perfluoroalkylation of Organobromides.有机溴化物的金属光氧化还原全氟烷基化反应
J Am Chem Soc. 2020 Nov 18;142(46):19480-19486. doi: 10.1021/jacs.0c09977. Epub 2020 Nov 9.
5
Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent.以2-三氟甲基苯并咪唑啉作为三氟甲基化试剂对碘芳烃进行催化三氟甲基化反应。
Beilstein J Org Chem. 2020 Sep 30;16:2442-2447. doi: 10.3762/bjoc.16.198. eCollection 2020.
6
Ruthenium-Catalyzed Site-Selective Trifluoromethylations and (Per)Fluoroalkylations of Anilines and Indoles.钌催化的苯胺和吲哚的位点选择性三氟甲基化和(全)氟烷基化反应。
Chemistry. 2020 May 26;26(30):6784-6788. doi: 10.1002/chem.202001439. Epub 2020 May 12.
7
Unusual Electronic Effects of Ancillary Ligands on the Perfluoroalkylation of Aryl Iodides and Bromides Mediated by Copper(I) Pentafluoroethyl Complexes of Substituted Bipyridines.取代联吡啶铜(I)五氟乙基配合物介导的芳基碘化物和溴化物的全氟烷基化反应中辅助配体的异常电子效应。
J Am Chem Soc. 2019 Dec 11;141(49):19458-19465. doi: 10.1021/jacs.9b10540. Epub 2019 Dec 2.
8
Aryl Sulfonium Salts for Site-Selective Late-Stage Trifluoromethylation.芳基锍盐用于选择性的晚期三氟甲基化反应。
Angew Chem Int Ed Engl. 2019 Oct 7;58(41):14615-14619. doi: 10.1002/anie.201906672. Epub 2019 Sep 4.
9
Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides.用于芳基碘化物三氟甲基化的明确铜试剂和前体的比较分析。
Beilstein J Org Chem. 2017 Oct 30;13:2297-2303. doi: 10.3762/bjoc.13.225. eCollection 2017.
10
Copper-Catalyzed Aerobic C-H Trifluoromethylation of Phenanthrolines.铜催化菲咯啉的需氧C-H三氟甲基化反应
Synlett. 2015;26(3):345-349. doi: 10.1055/s-0034-1379319.