• 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

通过钯催化剂活化惰性C(sp)-H键,使用二芳基碘鎓盐对肟醚进行芳基化反应。

-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)-H bonds using a palladium catalyst.

作者信息

Peng Jing, Chen Chao, Xi Chanjuan

机构信息

Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education) , Department of Chemistry , Tsinghua University , Beijing 100084 , China . Email:

出版信息

Chem Sci. 2016 Feb 1;7(2):1383-1387. doi: 10.1039/c5sc03903g. Epub 2015 Nov 11.

DOI:10.1039/c5sc03903g
PMID:29910895
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5975923/
Abstract

An efficient method of selective -arylation of oxime ethers was realized by using a palladium catalyst with diaryliodonium salts as the key arylation reagents. The reaction proceeded smoothly through the activation of inert C(sp)-H bonds to give corresponding ketones and aldehydes. This convenient procedure can be successfully applied to construct new C(sp)-C(sp) bonds on a number of complex molecules derived from natural products and thus serves as a practical synthetic tool for direct late-stage C(sp)-H functionalization.

摘要

通过使用钯催化剂和二芳基碘鎓盐作为关键芳基化试剂,实现了一种肟醚的高效选择性芳基化方法。该反应通过惰性C(sp) - H键的活化顺利进行,生成相应的酮和醛。这一简便方法能够成功应用于在许多源自天然产物的复杂分子上构建新的C(sp) - C(sp)键,因此可作为直接后期C(sp) - H官能团化的实用合成工具。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/62f80d067f80/c5sc03903g-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/ed4b10b3719b/c5sc03903g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/31ca43975a87/c5sc03903g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/10e9c81fe599/c5sc03903g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/6058f09645d1/c5sc03903g-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/183ed6a5ec05/c5sc03903g-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/398d91112dba/c5sc03903g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/db0b6652a2bc/c5sc03903g-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/03f616e0594e/c5sc03903g-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/62f80d067f80/c5sc03903g-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/ed4b10b3719b/c5sc03903g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/31ca43975a87/c5sc03903g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/10e9c81fe599/c5sc03903g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/6058f09645d1/c5sc03903g-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/183ed6a5ec05/c5sc03903g-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/398d91112dba/c5sc03903g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/db0b6652a2bc/c5sc03903g-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/03f616e0594e/c5sc03903g-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ff65/5975923/62f80d067f80/c5sc03903g-s8.jpg

相似文献

1
-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)-H bonds using a palladium catalyst.通过钯催化剂活化惰性C(sp)-H键,使用二芳基碘鎓盐对肟醚进行芳基化反应。
Chem Sci. 2016 Feb 1;7(2):1383-1387. doi: 10.1039/c5sc03903g. Epub 2015 Nov 11.
2
Iridium(III)-catalyzed direct arylation of C-H bonds with diaryliodonium salts.铱(III)催化的芳基碘盐与 C-H 键的直接芳基化反应。
J Am Chem Soc. 2015 Sep 30;137(38):12231-40. doi: 10.1021/jacs.5b06758. Epub 2015 Sep 22.
3
Direct arylation of C(sp3)-H bonds in aliphatic amides with diaryliodonium salts in the presence of a nickel catalyst.在镍催化剂存在下,脂肪族酰胺中C(sp3)-H键与二芳基碘鎓盐的直接芳基化反应。
J Org Chem. 2014 Dec 19;79(24):11933-9. doi: 10.1021/jo501691f. Epub 2014 Sep 4.
4
Direct functionalization processes: a journey from palladium to copper to iron to nickel to metal-free coupling reactions.直接官能团化反应:从钯到铜到铁到镍再到无金属偶联反应的历程。
Acc Chem Res. 2013 Feb 19;46(2):412-24. doi: 10.1021/ar300185z. Epub 2012 Oct 26.
5
Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts.使用二芳基碘鎓盐对杂芳烃进行无过渡金属后期C-H和N-H芳基化的最新进展
Pharmaceuticals (Basel). 2021 Jul 11;14(7):661. doi: 10.3390/ph14070661.
6
Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds.钯和铜催化的碳氢键芳基化反应。
Acc Chem Res. 2009 Aug 18;42(8):1074-86. doi: 10.1021/ar9000058.
7
C-2 selective arylation of indoles with heterogeneous nanopalladium and diaryliodonium salts.吲哚与非均相纳米钯和二芳基碘鎓盐的C-2选择性芳基化反应。
Chemistry. 2014 Oct 13;20(42):13531-5. doi: 10.1002/chem.201404017. Epub 2014 Aug 28.
8
Metal-Free and Open-Air Arylation Reactions of Diaryliodonium Salts for DNA-Encoded Library Synthesis.无金属和开放体系下二芳基碘鎓盐的芳基化反应在 DNA 编码化合物库合成中的应用。
Adv Sci (Weinh). 2022 Sep;9(26):e2202790. doi: 10.1002/advs.202202790. Epub 2022 Jul 19.
9
Iridium(iii)-catalyzed regioselective direct arylation of sp(2) C-H bonds with diaryliodonium salts.铱(III)催化的sp(2) C-H键与二芳基碘鎓盐的区域选择性直接芳基化反应。
Org Biomol Chem. 2016 Aug 7;14(29):7109-13. doi: 10.1039/c6ob01145d. Epub 2016 Jul 6.
10
Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.将过渡金属催化与自由基化学相结合:二芳基碘鎓盐显著加速钯催化的C-H芳基化反应
Adv Synth Catal. 2012 Dec 14;354(18):3517-3522. doi: 10.1002/adsc.201200738.

引用本文的文献

1
Total Synthesis of the Nominal Structure of (+)-Talaromyolide D.(+)-塔洛米利德D名义结构的全合成
J Am Chem Soc. 2025 Aug 27;147(34):31221-31227. doi: 10.1021/jacs.5c10325. Epub 2025 Aug 13.
2
Advances in α-Arylation of Carbonyl Compounds: Diaryliodonium Salts as Arylating Agents.羰基化合物的α-芳基化进展:以二芳基碘鎓盐作为芳基化试剂
Molecules. 2025 Jul 18;30(14):3019. doi: 10.3390/molecules30143019.
3
Pd-Catalyzed -C(sp)-H (Hetero)Arylation of Ketones Enabled by Transient Directing Groups.瞬态导向基团实现的钯催化酮的-C(sp)-H(杂)芳基化反应

本文引用的文献

1
Palladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: a stoichiometric heavy metal-free and user-friendly approach.钯催化酮与二芳基碘鎓盐的直接β-芳基化反应:一种无化学计量重金属且用户友好的方法。
Chem Sci. 2015 Oct 1;6(10):5491-5498. doi: 10.1039/c5sc01636c. Epub 2015 Jun 17.
2
Iridium(III)-catalyzed direct arylation of C-H bonds with diaryliodonium salts.铱(III)催化的芳基碘盐与 C-H 键的直接芳基化反应。
J Am Chem Soc. 2015 Sep 30;137(38):12231-40. doi: 10.1021/jacs.5b06758. Epub 2015 Sep 22.
3
Rhodium-Catalyzed Alkylation of C-H Bonds in Aromatic Amides with Styrenes via Bidentate-Chelation Assistance.
ACS Catal. 2022 Sep 2;12(17):10581-10586. doi: 10.1021/acscatal.2c03400. Epub 2022 Aug 15.
4
Transition-Metal-Catalyzed C-H Bond Activation for the Formation of C-C Bonds in Complex Molecules.过渡金属催化的 C-H 键活化在复杂分子中 C-C 键的形成。
Chem Rev. 2023 Jun 28;123(12):7692-7760. doi: 10.1021/acs.chemrev.2c00888. Epub 2023 May 10.
5
Wet carbonate-promoted radical arylation of vinyl pinacolboronates with diaryliodonium salts yields substituted olefins.湿碳酸根促进的乙烯基频哪醇硼酸酯与二芳基碘鎓盐的自由基芳基化反应生成取代烯烃。
Commun Chem. 2020 Jul 22;3(1):92. doi: 10.1038/s42004-020-00343-8.
6
Diverse reactivity of the gem-difluorovinyl iodonium salt for direct incorporation of the difluoroethylene group into N- and O-nucleophiles.偕二氟乙烯基碘鎓盐将二氟乙烯基直接引入 N- 和 O-亲核试剂的多样反应性。
Commun Chem. 2022 Dec 3;5(1):167. doi: 10.1038/s42004-022-00772-7.
7
Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp)-H Bonds.过渡金属催化的非活化 C(sp3)-H 键的配位辅助功能化。
Chem Rev. 2021 Dec 22;121(24):14957-15074. doi: 10.1021/acs.chemrev.1c00519. Epub 2021 Oct 29.
8
Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C-H activation.六氟异丙醇:钯催化C-H活化的神奇溶剂。
Chem Sci. 2021 Feb 10;12(11):3857-3870. doi: 10.1039/d0sc06937j.
9
Preparation and Synthetic Application of Naproxen-Containing Diaryliodonium Salts.含萘普生的二芳基碘鎓盐的制备及合成应用。
Molecules. 2021 May 28;26(11):3240. doi: 10.3390/molecules26113240.
10
A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.指导基团在金属催化 C-H 官能化化学中的应用综述。
Chem Soc Rev. 2018 Aug 28;47(17):6603-6743. doi: 10.1039/c8cs00201k.
铑催化的芳族酰胺中C-H键与苯乙烯通过双齿螯合辅助的烷基化反应。
Org Lett. 2015 Jul 17;17(14):3584-7. doi: 10.1021/acs.orglett.5b01682. Epub 2015 Jun 30.
4
Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.铜催化烯丙基酰胺与二芳基碘鎓盐的对映选择性和区域发散性亲电芳基化反应
J Am Chem Soc. 2015 Jul 1;137(25):7986-9. doi: 10.1021/jacs.5b03937. Epub 2015 Jun 19.
5
Cp*Ir(III)-Catalyzed Mild and Broad C-H Arylation of Arenes and Alkenes with Aryldiazonium Salts Leading to the External Oxidant-Free Approach.Cp*Ir(III)-催化的温和且广泛的芳基和烯烃的 C-H 芳基化反应与芳基重氮盐,无需外部氧化剂。
J Am Chem Soc. 2015 Jul 8;137(26):8584-92. doi: 10.1021/jacs.5b04043. Epub 2015 Jun 29.
6
Direct ortho-C-H functionalization of aromatic alcohols masked by acetone oxime ether via exo-palladacycle.通过外向钯环化反应实现丙酮肟醚掩蔽的芳香醇的直接邻位C-H官能化。
Org Lett. 2015 Apr 3;17(7):1802-5. doi: 10.1021/acs.orglett.5b00594. Epub 2015 Mar 13.
7
Palladium(II)-catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines.钯(II)催化的环丙基甲胺的高度对映选择性C-H芳基化反应。
J Am Chem Soc. 2015 Feb 11;137(5):2042-6. doi: 10.1021/ja512529e. Epub 2015 Jan 27.
8
Carbon-Hydrogen (C-H) Bond Activation at Pd: A Frontier in C-H Functionalization Catalysis.钯催化的碳-氢键活化:碳-氢键官能团化催化的前沿领域
Chem Sci. 2015 Jan;6(1):70-76. doi: 10.1039/C4SC02591A.
9
Transition-metal-free coupling reactions.无过渡金属偶联反应
Chem Rev. 2014 Sep 24;114(18):9219-80. doi: 10.1021/cr400274j. Epub 2014 Sep 3.
10
A palladium-catalyzed three-component-coupling strategy for the differential vicinal diarylation of terminal 1,3-dienes.一种用于末端1,3 - 二烯的选择性邻位双芳基化的钯催化三组分偶联策略。
Org Lett. 2014 Sep 5;16(17):4666-9. doi: 10.1021/ol502279u. Epub 2014 Aug 27.