自由基介导的乙烯基砜的硫代脱磺酰化反应：合成（α-氟）乙烯基硫醚
Radical-mediated thiodesulfonylation of the vinyl sulfones: Access to (α-fluoro)vinyl sulfides.
作者信息
Sacasa Pablo R, Zayas Jessica, Wnuk Stanislaw F
机构信息
Department of Chemistry and Biochemistry, Florida International University, Miami, Florida 33199, USA.
出版信息
Tetrahedron Lett. 2009 Sep 23;50(38):5424-5427. doi: 10.1016/j.tetlet.2009.07.063.
Abstract
Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.
摘要
在有机或水性介质中，由醛和酮衍生的乙烯基和（α-氟）乙烯基砜与芳基硫醇进行自由基介导的硫代脱磺酰化反应，可得到乙烯基和（α-氟）乙烯基硫醚。乙烯基硫醚主要以E构型形成，与起始乙烯基砜的立体化学无关。
相似文献
1
Radical-mediated thiodesulfonylation of the vinyl sulfones: Access to (α-fluoro)vinyl sulfides.自由基介导的乙烯基砜的硫代脱磺酰化反应：合成（α-氟）乙烯基硫醚
Tetrahedron Lett. 2009 Sep 23;50(38):5424-5427. doi: 10.1016/j.tetlet.2009.07.063.
2
Radical-mediated silyl- and germyldesulfonylation of vinyl and (alpha-fluoro)vinyl sulfones: application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings.自由基介导的乙烯基和（α-氟）乙烯基砜的硅基化和锗基脱磺酰化反应：三（三甲基硅基）硅烷和三（三甲基硅基）锗烷在钯催化偶联反应中的应用
Org Lett. 2004 Jun 10;6(12):2047-9. doi: 10.1021/ol049312n.
3
The Z-enoate Assisted Meyer-Schuster Rearrangement With Thiol Nucleophiles: An Approach for the Functionalized Vinyl Sulfides and Sulfones.
Chem Asian J. 2025 Jun;20(12):e202500080. doi: 10.1002/asia.202500080. Epub 2025 Apr 28.
4
Sodium iodide-mediated synthesis of vinyl sulfides and vinyl sulfones with solvent-controlled chemical selectivity.碘化钠介导的乙烯基硫醚和乙烯基砜的合成及其溶剂控制的化学选择性
RSC Adv. 2021 Oct 31;11(56):35156-35160. doi: 10.1039/d1ra07086j. eCollection 2021 Oct 28.
5
Atom- and step-economic 1,3-thiosulfonylation of activated allenes with thiosulfonates to access vinyl sulfones/sulfides.原子经济性和步骤经济性的 1,3-硫代磺酰化反应，使用硫代硫酸盐对活化的丙二烯进行硫代磺酰化反应，以获得乙烯基砜/硫醚。
Chem Commun (Camb). 2022 Jun 9;58(47):6765-6768. doi: 10.1039/d2cc01731h.
6
A photocatalyst-free visible-light-mediated solvent-switchable route to stilbenes/vinyl sulfones from β-nitrostyrenes and arylazo sulfones.一种无光催化剂的可见光介导的溶剂可切换路线，用于从β-硝基苯乙烯和芳基偶氮砜制备二苯乙烯/乙烯基砜。
Org Biomol Chem. 2021 Jul 28;19(29):6487-6492. doi: 10.1039/d1ob01028j.
7
Formyl Radical Generation from α-Chloro N-Methoxyphthalimides Enables Selective Aldehyde Synthesis.α-氯-N-甲氧基邻苯二甲酰亚胺产生甲酰基自由基，实现选择性醛合成。
Angew Chem Int Ed Engl. 2023 Jan 2;62(1):e202213686. doi: 10.1002/anie.202213686. Epub 2022 Nov 29.
8
Access to spirocyclic vinyl sulfones radical cyclization and functional group migration.获得螺环乙烯基砜的自由基环化和官能团迁移。
Chem Sci. 2025 Apr 29. doi: 10.1039/d5sc02555a.
9
A benzannulation protocol to prepare substituted aryl amines using a Michael-aldol reaction of beta-keto sulfones.一种使用β-酮砜的迈克尔-羟醛反应制备取代芳基胺的苯并环化方法。
J Org Chem. 2009 Oct 16;74(20):7781-9. doi: 10.1021/jo9017793.
10
Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones.无金属促进的芳基烯烃与硫醇的氧化偶联反应生成（E）-乙烯基砜。
J Org Chem. 2017 Jul 7;82(13):6857-6864. doi: 10.1021/acs.joc.7b00994. Epub 2017 Jun 22.
引用本文的文献
1
Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions.温和且无过渡金属条件下硫醇的亲电乙烯基化反应
Angew Chem Int Ed Engl. 2020 Sep 1;59(36):15512-15516. doi: 10.1002/anie.202002936. Epub 2020 Jun 15.
2
Synthesis and Deployment of an Elusive Fluorovinyl Cation Equivalent: Access to Quaternary α-(1'-Fluoro)vinyl Amino Acids as Potential PLP Enzyme Inactivators.合成和部署难以捉摸的氟乙烯基阳离子等价物：获得潜在的 PLP 酶失活剂作为四元α-（1'-氟）乙烯基氨基酸。
J Am Chem Soc. 2017 Oct 11;139(40):14077-14089. doi: 10.1021/jacs.7b04690. Epub 2017 Sep 28.
3
Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers.路易斯酸促进的炔基硫醚氢氟化反应生成α-氟代乙烯基硫醚。
Beilstein J Org Chem. 2015 Oct 14;11:1902-9. doi: 10.3762/bjoc.11.205. eCollection 2015.
本文引用的文献
1
Stereo- and regiospecific cu-catalyzed cross-coupling reaction of vinyl iodides and thiols: a very mild and general route for the synthesis of vinyl sulfides.铜催化的立体和区域特异性碘乙烯与硫醇的交叉偶联反应：一种非常温和且通用的合成乙烯基硫醚的方法。
Org Lett. 2008 Aug 7;10(15):3363-6. doi: 10.1021/ol801149n. Epub 2008 Jul 9.
2
Radical reactions in aqueous medium using (Me3Si)3SiH.使用(Me3Si)3SiH在水介质中的自由基反应。
Org Lett. 2007 Dec 6;9(25):5159-62. doi: 10.1021/ol7020803. Epub 2007 Nov 13.
3
New approach for size- and shape-controlled preparation of Pd nanoparticles with organic ligands. Synthesis and application in catalysis.利用有机配体控制钯纳米粒子尺寸和形状的新方法。合成及其在催化中的应用。
J Am Chem Soc. 2007 Jun 13;129(23):7252-3. doi: 10.1021/ja071727r. Epub 2007 May 19.
4
Vinyl sulfones: synthetic preparations and medicinal chemistry applications.乙烯砜：合成制备及药物化学应用
Med Res Rev. 2006 Nov;26(6):793-814. doi: 10.1002/med.20074.
5
Organosulfur compounds: electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions.有机硫化合物：过渡金属催化的碳-碳键形成反应中的亲电试剂。
Angew Chem Int Ed Engl. 2005 Dec 2;44(47):7674-84. doi: 10.1002/anie.200463007.
6
Radical-mediated silyl- and germyldesulfonylation of vinyl and (alpha-fluoro)vinyl sulfones: application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings.自由基介导的乙烯基和（α-氟）乙烯基砜的硅基化和锗基脱磺酰化反应：三（三甲基硅基）硅烷和三（三甲基硅基）锗烷在钯催化偶联反应中的应用
Org Lett. 2004 Jun 10;6(12):2047-9. doi: 10.1021/ol049312n.
7
Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones.1-炔基亚砜或砜的氢锆化反应研究及其在立体定向乙烯基亚砜或砜合成中的应用。
J Org Chem. 2003 Mar 7;68(5):1958-63. doi: 10.1021/jo0111154.
8
9
Metal-catalyzed carbon-sulfur bond formation.金属催化的碳-硫键形成。
Chem Rev. 2000 Aug 9;100(8):3205-20. doi: 10.1021/cr9902749.
10
Coupling of 2-Substituted 1-Fluorovinylstannanes with Organic Halides Catalyzed by Palladium(0)/Copper(I) Iodide. A Mild and Stereospecific Method to Monofluoroolefins.钯(0)/碘化亚铜催化的2-取代1-氟乙烯基锡烷与有机卤化物的偶联反应：一种制备单氟烯烃的温和且立体专一性方法
J Org Chem. 1999 May 14;64(10):3476-3482. doi: 10.1021/jo982200n.
Zotero 插件