• 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

镍催化三氟甲基烯烃的烯丙基脱氟烷基化反应与氧化还原活性酯的还原脱羧反应。

Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters.

作者信息

Lu Xi, Wang Xiao-Xu, Gong Tian-Jun, Pi Jing-Jing, He Shi-Jiang, Fu Yao

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale , CAS Key Laboratory of Urban Pollutant Conversion , Anhui Province Key Laboratory of Biomass Clean Energy , iChEM , University of Science and Technology of China , Hefei 230026 , China . Email:

出版信息

Chem Sci. 2018 Nov 7;10(3):809-814. doi: 10.1039/c8sc04335c. eCollection 2019 Jan 21.

DOI:10.1039/c8sc04335c
PMID:30774875
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6345349/
Abstract

Herein, we report a nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes through reductive decarboxylation of redox-active esters. The present reaction enables the preparation of functionalized -difluoroalkenes with the formation of sterically hindered C(sp)-C(sp) bonds under very mild reaction conditions, while tolerating many sensitive functional groups and requiring minimal substrate protection. Therefore, this method provides an efficient and convenient approach for late-stage modification of biologically interesting molecules.

摘要

在此,我们报道了一种通过氧化还原活性酯的还原脱羧实现的镍催化三氟甲基烯烃的烯丙基脱氟烷基化反应。本反应能够在非常温和的反应条件下制备官能化的二氟烯烃,并形成空间位阻较大的C(sp³)-C(sp³)键,同时耐受许多敏感官能团且所需的底物保护最少。因此,该方法为具有生物学意义的分子的后期修饰提供了一种高效便捷的途径。

相似文献

1
Nickel-catalyzed allylic defluorinative alkylation of trifluoromethyl alkenes with reductive decarboxylation of redox-active esters.镍催化三氟甲基烯烃的烯丙基脱氟烷基化反应与氧化还原活性酯的还原脱羧反应。
Chem Sci. 2018 Nov 7;10(3):809-814. doi: 10.1039/c8sc04335c. eCollection 2019 Jan 21.
2
Synthesis of gem-difluoroalkenes via nickel-catalyzed allylic defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides.通过镍催化的三氟甲基烯烃与环氧化物的烯丙基脱氟还原交叉偶联合成偕二氟烯烃。
Org Biomol Chem. 2020 May 20;18(19):3674-3678. doi: 10.1039/d0ob00535e.
3
Electroreductive Cross-Coupling of Trifluoromethyl Alkenes and Redox Active Esters for the Synthesis of Gem-Difluoroalkenes.三氟乙烯基与氧化还原活性酯的电化学交叉偶联反应在全氟烯烃合成中的应用。
Chemistry. 2022 Jan 10;28(2):e202103337. doi: 10.1002/chem.202103337. Epub 2021 Nov 16.
4
Nickel-Catalyzed Defluorinative Reductive Cross-Coupling of gem-Difluoroalkenes with Unactivated Secondary and Tertiary Alkyl Halides.镍催化的全氟烯烃与非活化仲烷基和叔烷基卤化物的脱氟还原交叉偶联反应。
J Am Chem Soc. 2017 Sep 13;139(36):12632-12637. doi: 10.1021/jacs.7b06469. Epub 2017 Aug 29.
5
Photoredox-Catalyzed Allylic Defluorinative Alkoxycarbonylation of Trifluoromethyl Alkenes through Intermolecular Alkoxycarbonyl Radical Addition.通过分子间烷氧基羰基自由基加成实现光氧化还原催化三氟甲基烯烃的烯丙位脱氟烷氧基羰基化反应。
Org Lett. 2022 Feb 25;24(7):1471-1475. doi: 10.1021/acs.orglett.1c04359. Epub 2022 Feb 15.
6
Nickel-Catalyzed Allylic Defluorinative Cross-Electrophile Coupling with Cycloalkyl Silyl Peroxides as the Alkyl Source.镍催化烯丙基脱氟交叉电偶联反应:环烷基硅基过氧化物作为烷基源。
J Org Chem. 2022 Jan 7;87(1):892-903. doi: 10.1021/acs.joc.1c02674. Epub 2021 Dec 27.
7
Merger of C-F and C-N Bond Cleavage in Cross-Electrophile Coupling for the Synthesis of -Difluoroalkenes.C-F 和 C-N 键的交叉亲电偶联断裂在 -二氟烯烃合成中的应用。
Org Lett. 2020 Jul 17;22(14):5347-5352. doi: 10.1021/acs.orglett.0c01592. Epub 2020 Jun 26.
8
Reductive Allylic Defluorinative Cross-Coupling Enabled by Ni/Ti Cooperative Catalysis.镍/钛协同催化实现还原烯丙基脱氟交叉偶联反应。
Org Lett. 2019 Oct 18;21(20):8316-8322. doi: 10.1021/acs.orglett.9b03102. Epub 2019 Oct 1.
9
Nickel-Catalyzed Ligand-Controlled Selective Reductive Cyclization/Cross-Couplings.镍催化的配体控制的选择性还原环化/交叉偶联反应
Acc Chem Res. 2023 Mar 7;56(5):515-535. doi: 10.1021/acs.accounts.2c00771. Epub 2023 Jan 23.
10
Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.镍催化脂肪醛与三氟甲基烯烃的脱氟偶联反应
ACS Catal. 2022 Feb 18;12(4):2463-2471. doi: 10.1021/acscatal.1c05801. Epub 2022 Feb 3.

引用本文的文献

1
Redox-neutral photocatalytic cleavage and -difluoroalkenylation of lignin linkages.木质素键的氧化还原中性光催化裂解和二氟烯基化反应
Sci Adv. 2025 Aug 15;11(33):eady2227. doi: 10.1126/sciadv.ady2227.
2
Continuous Flow Decarboxylative Monofluoroalkylation Enabled by Photoredox Catalysis.光氧化还原催化实现的连续流动脱羧单氟烷基化反应
JACS Au. 2025 Feb 2;5(2):684-692. doi: 10.1021/jacsau.4c00902. eCollection 2025 Feb 24.
3
Chemodivergent alkylation of trifluoromethyl alkenes photocatalytic coupling with alkanes.三氟甲基烯烃的化学发散烷基化:与烷烃的光催化偶联

本文引用的文献

1
Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis.钴催化氧化还原活性脂肪族酯的脱羧Negishi偶联反应
Angew Chem Int Ed Engl. 2018 Oct 1;57(40):13096-13100. doi: 10.1002/anie.201806799. Epub 2018 Sep 4.
2
A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.由固有自由基交叉偶联作用实现的一般氨基酸合成。
Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14560-14565. doi: 10.1002/anie.201809310. Epub 2018 Oct 15.
3
Organocatalytic decarboxylative alkylation of N-hydroxy-phthalimide esters enabled by pyridine-boryl radicals.
Green Chem. 2024 Oct 4;26(22):11196-11205. doi: 10.1039/d4gc04176c. eCollection 2024 Nov 11.
4
Nickel-catalyzed regiodivergent hydrosilylation of α-(fluoroalkyl)styrenes without defluorination.镍催化α-(氟烷基)苯乙烯的区域发散性硅氢化反应且无脱氟现象。
Nat Commun. 2024 Jul 28;15(1):6360. doi: 10.1038/s41467-024-50743-w.
5
Synthesis of alcohols: streamlined C1 to C hydroxyalkylation through photoredox catalysis.醇的合成:通过光氧化还原催化实现从C1到C的简化羟基烷基化反应
Chem Sci. 2024 Jun 13;15(29):11337-11346. doi: 10.1039/d4sc02696a. eCollection 2024 Jul 24.
6
A review of frustrated Lewis pair enabled monoselective C-F bond activation.受阻路易斯酸碱对实现单选择性碳氟键活化的综述。
Chem Sci. 2024 Jan 16;15(8):2712-2724. doi: 10.1039/d3sc06485a. eCollection 2024 Feb 22.
7
Nickel-Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α-Amino Ketones.镍催化对映选择性脱羧酰化反应:快速、模块化合成α-氨基酮
Angew Chem Int Ed Engl. 2023 Dec 11;62(50):e202315203. doi: 10.1002/anie.202315203. Epub 2023 Nov 16.
8
Stereospecific Nickel-Catalyzed Cross-Electrophile Coupling Reaction of Alkyl Mesylates and Allylic Difluorides to Access Enantioenriched Vinyl Fluoride-Substituted Cyclopropanes.立体专一性镍催化的甲磺酸烷基酯与烯丙基二氟化物的交叉亲电偶联反应,用于合成对映体富集的氟乙烯取代环丙烷。
ACS Catal. 2023 Mar 20;13(7):4488-4499. doi: 10.1021/acscatal.3c00257. eCollection 2023 Apr 7.
9
Experimental and computational insights into the mechanism of FLP mediated selective C-F bond activation.关于FLP介导的选择性C-F键活化机制的实验与计算见解
Chem Sci. 2023 Jan 13;14(5):1291-1300. doi: 10.1039/d2sc05632a. eCollection 2023 Feb 1.
10
Electrochemical Synthesis of gem-Difluoro- and γ-Fluoro-Allyl Boronates and Silanes.电化学合成偕二氟-和γ-氟代烯丙基硼酸盐和硅烷。
Chemistry. 2022 Nov 25;28(66):e202202194. doi: 10.1002/chem.202202194. Epub 2022 Sep 26.
通过吡啶硼基自由基实现 N-羟基邻苯二甲酰亚胺酯的有机催化脱羧烷基化反应。
Chem Commun (Camb). 2018 Oct 11;54(82):11534-11537. doi: 10.1039/c8cc06152a.
4
Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay.镍催化还原自由基接力实现烯烃的分子间选择性碳酰化反应。
Nat Commun. 2018 Aug 28;9(1):3488. doi: 10.1038/s41467-018-05951-6.
5
Metallaphotoredox Difluoromethylation of Aryl Bromides.金属光氧化还原二氟甲基化芳基溴化物。
Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12543-12548. doi: 10.1002/anie.201807629. Epub 2018 Aug 28.
6
Zinc-Mediated Decarboxylative Alkylation of Gem-difluoroalkenes.锌介导的偕二氟烯烃的脱羧烷基化反应。
Org Lett. 2018 Aug 3;20(15):4579-4583. doi: 10.1021/acs.orglett.8b01866. Epub 2018 Jul 19.
7
Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents.使用芳基硼酸酯活化的烷基格氏试剂进行对映选择性铜催化的脱氟烷基化反应
J Am Chem Soc. 2018 Jul 25;140(29):9061-9065. doi: 10.1021/jacs.8b04902. Epub 2018 Jul 10.
8
Transition-Metal-Mediated and -Catalyzed C-F Bond Activation by Fluorine Elimination.通过氟消除实现的过渡金属介导和催化的C-F键活化
Angew Chem Int Ed Engl. 2019 Jan 8;58(2):390-402. doi: 10.1002/anie.201805292. Epub 2018 Nov 8.
9
Picking One out of Three: Selective Single C-F Activation in Trifluoromethyl Groups.三选一:三氟甲基中 C-F 的选择性单键活化。
Chemistry. 2018 Oct 1;24(55):14572-14582. doi: 10.1002/chem.201801702. Epub 2018 Jul 30.
10
Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis.通过镍催化实现草酸苄酯与高度官能化烷基溴的还原偶联反应。
Chem Sci. 2018 Apr 20;9(19):4529-4534. doi: 10.1039/c8sc00609a. eCollection 2018 May 21.