• 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Julia-Kocienski烯烃化反应合成氟代烯烃

Synthesis of Fluoroolefins via Julia-Kocienski Olefination.

作者信息

Zajc Barbara, Kumar Rakesh

机构信息

Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031.

出版信息

Synthesis (Stuttg). 2010;2010(11):1822-1836. doi: 10.1055/s-0029-1218789.

DOI:10.1055/s-0029-1218789
PMID:22544979
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3337086/
Abstract

The Julia-Kocienski olefination provides a versatile platform for the synthesis of fluorovinyl compounds. This review describes our efforts as well as those of others in the synthesis of various fluorinated aryl and heteroaryl sulfones and their utility as olefination reagents for the modular assembly of fluoroalkenes. Where data is available, the influence of the fluorine atom on the reactivity of the olefination reagents and the stereochemical outcome of the olefination are described.

摘要

Julia-Kocienski烯化反应为氟乙烯基化合物的合成提供了一个通用平台。本综述描述了我们以及其他人在合成各种氟化芳基和杂芳基砜方面的努力，以及它们作为氟烯烃模块化组装的烯化试剂的用途。在有数据的情况下，描述了氟原子对烯化试剂反应性和烯化反应立体化学结果的影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/b4d955bf86f8/nihms276485f38.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/056034e9cdac/nihms276485f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/3e7d7db3b200/nihms276485f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/5ae192f90a84/nihms276485f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/578ccbd0e952/nihms276485f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/fd093138e627/nihms276485f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/883f112ad0f5/nihms276485f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/6b0f7df700b2/nihms276485f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/f638ad5c0fbb/nihms276485f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/430e7854ab0e/nihms276485f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/1ab7a35f591f/nihms276485f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/35a816003f19/nihms276485f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/185c1baa33f1/nihms276485f12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/b307ce5bec73/nihms276485f13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/c77e2599e881/nihms276485f14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/f063b17046f2/nihms276485f15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/c152ae7ea941/nihms276485f16.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/4ed02aeb5a27/nihms276485f17.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/9cfafe949304/nihms276485f18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/da3d4c0d364c/nihms276485f19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/a0bc6460058e/nihms276485f20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/e36f1e5500fd/nihms276485f21.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/028e8babb8fb/nihms276485f22.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/c4def2fe4302/nihms276485f23.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/920acdc93f2b/nihms276485f24.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/adfd1368e16a/nihms276485f25.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/f325e82402df/nihms276485f26.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/4a18274217bd/nihms276485f27.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/75516626ab2c/nihms276485f28.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/d02c4ec60549/nihms276485f29.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/8b591c710e32/nihms276485f30.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/59744425fe31/nihms276485f31.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/5c45d1515b99/nihms276485f32.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/6ac950df3939/nihms276485f33.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/33e289f0006f/nihms276485f34.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/e2209920f298/nihms276485f35.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/45f16ca17231/nihms276485f36.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/8c7b5389fe77/nihms276485f37.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/b4d955bf86f8/nihms276485f38.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/056034e9cdac/nihms276485f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/3e7d7db3b200/nihms276485f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/5ae192f90a84/nihms276485f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/578ccbd0e952/nihms276485f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/fd093138e627/nihms276485f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/883f112ad0f5/nihms276485f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/6b0f7df700b2/nihms276485f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/f638ad5c0fbb/nihms276485f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/430e7854ab0e/nihms276485f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/1ab7a35f591f/nihms276485f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/35a816003f19/nihms276485f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/185c1baa33f1/nihms276485f12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/b307ce5bec73/nihms276485f13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/c77e2599e881/nihms276485f14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/f063b17046f2/nihms276485f15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/c152ae7ea941/nihms276485f16.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/4ed02aeb5a27/nihms276485f17.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/9cfafe949304/nihms276485f18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/da3d4c0d364c/nihms276485f19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/a0bc6460058e/nihms276485f20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/e36f1e5500fd/nihms276485f21.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/028e8babb8fb/nihms276485f22.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/c4def2fe4302/nihms276485f23.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/920acdc93f2b/nihms276485f24.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/adfd1368e16a/nihms276485f25.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/f325e82402df/nihms276485f26.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/4a18274217bd/nihms276485f27.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/75516626ab2c/nihms276485f28.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/d02c4ec60549/nihms276485f29.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/8b591c710e32/nihms276485f30.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/59744425fe31/nihms276485f31.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/5c45d1515b99/nihms276485f32.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/6ac950df3939/nihms276485f33.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/33e289f0006f/nihms276485f34.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/e2209920f298/nihms276485f35.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/45f16ca17231/nihms276485f36.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/8c7b5389fe77/nihms276485f37.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/529f/3337086/b4d955bf86f8/nihms276485f38.jpg

相似文献

1
Synthesis of Fluoroolefins via Julia-Kocienski Olefination.通过Julia-Kocienski烯烃化反应合成氟代烯烃
Synthesis (Stuttg). 2010;2010(11):1822-1836. doi: 10.1055/s-0029-1218789.
2
3,5-bis(trifluoromethyl)phenyl sulfones in the direct Julia-Kocienski olefination.3,5-双（三氟甲基）苯砜在直接Julia-Kocienski烯烃化反应中的应用
J Org Chem. 2005 Aug 5;70(16):6404-16. doi: 10.1021/jo050852n.
3
Facile synthesis of 4-vinyl- and 4-fluorovinyl-1,2,3-triazoles via bifunctional "click-olefination" reagents.通过双功能“点击-烯烃化”试剂，简便地合成 4-乙烯基-和 4-氟乙烯基-1,2,3-三唑。
Chem Commun (Camb). 2011 Apr 7;47(13):3891-3. doi: 10.1039/c0cc05083k. Epub 2011 Feb 18.
4
E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents.使用氟化第二代朱莉娅-科琴斯基试剂进行4-氟乙烯基-1,2,3-三唑的E-或Z-选择性合成。
Org Biomol Chem. 2015 Feb 7;13(5):1536-49. doi: 10.1039/c4ob02179g.
5
A chain extension method for apocarotenoids; lycopene and lycophyll syntheses.一种类胡萝卜素的链延伸方法；番茄红素和番茄叶红素的合成。
Arch Biochem Biophys. 2015 Apr 15;572:142-150. doi: 10.1016/j.abb.2014.12.028. Epub 2015 Jan 8.
6
Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape.通过 Julia-Kocienski 烯烃化和氧化光环化反应实现区域特异性氟化多环芳烃。氟原子取代对分子形状的影响。
J Org Chem. 2016 May 20;81(10):3983-93. doi: 10.1021/acs.joc.5b02580. Epub 2016 Mar 22.
7
Stereoselective Olefination with Sterically Demanding Julia-Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B.使用空间位阻较大的Julia-Kocienski试剂进行立体选择性烯烃化反应：氧代原蒽环素、氧代托马霉素和宝城氮杂卓B的全合成
ACS Omega. 2022 Aug 17;7(34):30519-30534. doi: 10.1021/acsomega.2c03732. eCollection 2022 Aug 30.
8
Latest Developments of the Julia-Kocienski Olefination Reaction: Mechanistic Considerations.朱莉娅-科钦斯基烯烃化反应的最新进展：机理探讨
Molecules. 2024 Jun 7;29(12):2719. doi: 10.3390/molecules29122719.
9
Synthesis of regiospecifically fluorinated conjugated dienamides.区域特异性氟化共轭二烯酰胺的合成。
Molecules. 2014 Apr 10;19(4):4418-32. doi: 10.3390/molecules19044418.
10
Stereoselective Synthesis of Trisubstituted ()-Alkenes from Ketones via the Julia-Kocienski Olefination Using 1-Methyl- and 1--Butyl-1-tetrazol-5-yl Alkyl Sulfones.通过使用 1-甲基-和 1-丁基-1-四唑-5-基烷基砜的 Julia-Kocienski 烯烃化反应，从酮立体选择性合成三取代的 ()-烯烃。
Org Lett. 2020 Sep 4;22(17):6907-6910. doi: 10.1021/acs.orglett.0c02440. Epub 2020 Aug 21.

引用本文的文献

1
HO as the Hydrogen Donor: Stereo-Selective Synthesis of - and -Alkenes by Palladium-Catalyzed Semihydrogenation of Alkynes.以氢作为氢供体：通过钯催化炔烃的半氢化反应立体选择性合成α-和β-烯烃。
ACS Omega. 2023 Mar 17;8(12):11492-11502. doi: 10.1021/acsomega.3c00287. eCollection 2023 Mar 28.
2
Stereoselective Synthesis of Tri- and Tetrasubstituted Olefins via 1,6-Additions of Diazo Compounds and Their Precursors to -Quinone Methides.通过重氮化合物及其前体对醌甲基化物的1,6-加成反应立体选择性合成三取代和四取代烯烃。
ACS Org Inorg Au. 2021 Aug 11;1(2):51-59. doi: 10.1021/acsorginorgau.1c00012. eCollection 2021 Dec 1.
3

本文引用的文献

1
The smiles rearrangement and the julia-kocienski olefination reaction.斯迈尔斯重排反应和朱利亚-科琴斯基烯烃化反应。
Top Curr Chem. 2007;275:163-250. doi: 10.1007/128_049.
2
Difluoromethyl 2-pyridyl sulfone: a new gem-difluoroolefination reagent for aldehydes and ketones.二氟甲基 2-吡啶砜：一种用于醛酮的新型偕二氟烯烃化试剂。
Org Lett. 2010 Apr 2;12(7):1444-7. doi: 10.1021/ol100090r.
3
Convenient electrophilic fluorination of functionalized aryl and heteroaryl magnesium reagents.功能化芳基和杂芳基镁试剂的便捷亲电氟化反应。
Au(I) Catalyzed HF Transfer: Tandem Alkyne Hydrofluorination and Perfluoroarene Functionalization.
金（I）催化的氢氟酸转移：串联炔烃氢氟化和全氟芳烃官能化
ACS Catal. 2022 Mar 18;12(6):3411-3419. doi: 10.1021/acscatal.1c05474. Epub 2022 Mar 1.
4
Palladium-Catalyzed Cross-Coupling of -Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes.钯催化 - 溴代氟烯与烷基硼酸的交叉偶联反应合成烷基单氟烯烃。
Molecules. 2020 Nov 25;25(23):5532. doi: 10.3390/molecules25235532.
5
Copper-Catalyzed Defluorinative Borylation and Silylation of -Difluoroallyl Groups.铜催化的脱氟硼化和硅烷化反应。
Org Lett. 2020 Sep 4;22(17):6805-6809. doi: 10.1021/acs.orglett.0c02321. Epub 2020 Aug 25.
6
Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents.使用质子化四氟硼酸盐作为可调试剂的立体发散炔烃氢氟化反应。
Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16651-16660. doi: 10.1002/anie.202006278. Epub 2020 Jul 14.
7
Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks.生成立体多样性：α-氨基酸砌块的非对映选择性氟化和高度非对映选择性差向异构化。
Org Lett. 2018 Jun 15;20(12):3574-3578. doi: 10.1021/acs.orglett.8b01358. Epub 2018 Jun 1.
8
Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres.基于单氟烯烃的二肽类似物的外消旋和对映选择性合成的最新进展。
Beilstein J Org Chem. 2017 Dec 12;13:2637-2658. doi: 10.3762/bjoc.13.262. eCollection 2017.
9
Divergent reactivities in fluoronation of allylic alcohols: synthesis of -fluoroalkenes carbon-carbon bond cleavage.烯丙醇氟化反应中的不同反应性：-氟代烯烃的合成与碳-碳键断裂
Chem Sci. 2017 May 1;8(5):3885-3890. doi: 10.1039/c7sc00483d. Epub 2017 Mar 20.
10
Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape.通过 Julia-Kocienski 烯烃化和氧化光环化反应实现区域特异性氟化多环芳烃。氟原子取代对分子形状的影响。
J Org Chem. 2016 May 20;81(10):3983-93. doi: 10.1021/acs.joc.5b02580. Epub 2016 Mar 22.
Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2215-8. doi: 10.1002/anie.200905052.
4
2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide: a reagent for nucleophilic monofluoromethylation of aldehydes.2-氟-1,3-苯并二硫醇-1,1,3,3-四氧化物：一种用于醛的亲核单氟甲基化的试剂。
Angew Chem Int Ed Engl. 2010 Feb 22;49(9):1642-7. doi: 10.1002/anie.200906866.
5
Use of task-specific ionic liquid for selective electrocatalytic fluorination.使用特定任务的离子液体进行选择性电催化氟化。
Org Lett. 2010 Feb 5;12(3):644-6. doi: 10.1021/ol9028836.
6
Efficient synthesis of aryl fluorides.芳基氟化物的高效合成。
Angew Chem Int Ed Engl. 2010 Mar 15;49(12):2219-22. doi: 10.1002/anie.200905855.
7
Toward the synthesis of benzothiazolyl fluoroaminosulfones.朝着苯并噻唑基氟氨基砜的合成。
J Org Chem. 2009 Dec 18;74(24):9399-405. doi: 10.1021/jo901540c.
8
Julia Olefination as a General Route to Phenyl (alpha-Fluoro)vinyl Sulfones.Julia烯化反应作为合成苯基（α-氟）乙烯基砜的通用方法。
Synlett. 2008 Apr 1;2008(7):999-1004. doi: 10.1055/s-2008-1072513.
9
Fluorinated 1-phenyl-1H-tetrazol-5-yl sulfone derivatives as general reagents for fluoroalkylidene synthesis.全氟亚甲基合成的通用试剂：氟化 1-苯基-1H-四唑-5-基砜衍生物。
J Org Chem. 2009 Nov 20;74(22):8531-40. doi: 10.1021/jo901313k.
10
Use of Fluorinated Functionality in Enzyme Inhibitor Development: Mechanistic and Analytical Advantages.氟代官能团在酶抑制剂开发中的应用：机理及分析优势
J Fluor Chem. 2008 Sep;129(9):731-742. doi: 10.1016/j.jfluchem.2008.05.016.