铑催化的通过异吲哚酮的C-C活化与炔烃进行的脱羰偶联反应。
Rh-Catalyzed decarbonylative coupling with alkynes via C-C activation of isatins.
作者信息
Zeng Rong, Dong Guangbin
机构信息
Department of Chemistry, University of Texas at Austin , Austin, Texas 78712, United States.
出版信息
J Am Chem Soc. 2015 Feb 4;137(4):1408-11. doi: 10.1021/ja512306a. Epub 2015 Jan 15.
Abstract
Herein we report a [5 + 2 - 1] transformation though catalytic decarbonylative coupling between isatins and alkynes, which provides a unique way to synthesize 2-quinolinone derivatives. A broad range of alkynes can be coupled efficiently with high regioselectivity. This reaction is proposed to go through C-C activation of isatins, followed by decarbonylation and alkyne insertion. Directing group (DG) plays a critical role in this transformation. Assisted by the DG, the C-C cleavage of isatins occurs at room temperature.
摘要
在此，我们报道了一种通过异吲哚酮与炔烃之间的催化脱羰偶联实现的[5 + 2 - 1]转化，该转化为合成2-喹啉酮衍生物提供了一种独特的方法。多种炔烃能够以高区域选择性高效偶联。该反应被认为是先通过异吲哚酮的C-C活化，然后进行脱羰和炔烃插入。导向基团（DG）在这一转化过程中起着关键作用。在导向基团的协助下，异吲哚酮的C-C裂解在室温下发生。
相似文献
1
Rh-Catalyzed decarbonylative coupling with alkynes via C-C activation of isatins.铑催化的通过异吲哚酮的C-C活化与炔烃进行的脱羰偶联反应。
J Am Chem Soc. 2015 Feb 4;137(4):1408-11. doi: 10.1021/ja512306a. Epub 2015 Jan 15.
2
Rhodium-catalyzed C-H activation of hydrazines leads to isoquinolones with tunable aggregation-induced emission properties.铑催化的肼的C-H活化反应可生成具有可调节聚集诱导发光特性的异喹啉酮。
Chem Commun (Camb). 2015 Oct 1;51(76):14365-8. doi: 10.1039/c5cc05239d. Epub 2015 Aug 13.
3
Rhodium(II) catalyzed diastereoselective reactions of diazoacetamides with isatins: an efficient approach to 3-hydroxy-3,3'-bioxindoles.铑(II)催化重氮乙酰胺与色酮的非对映选择性反应：合成 3-羟基-3,3'-联吲哚的有效方法。
Org Biomol Chem. 2012 Nov 28;10(44):8808-13. doi: 10.1039/c2ob26580j.
4
Rhodium(III)-catalyzed isoquinolone synthesis: the N-O bond as a handle for C-N bond formation and catalyst turnover.铑(III)催化的异喹啉合成：N-O 键作为 C-N 键形成和催化剂转化的关键。
J Am Chem Soc. 2010 May 26;132(20):6908-9. doi: 10.1021/ja102571b.
5
Synthesis of 1,1-disubstituted alkyl vinyl sulfides via rhodium-catalyzed alkyne hydrothiolation: scope and limitations.通过铑催化的炔烃氢硫基化反应合成1,1-二取代烷基乙烯基硫醚：范围和局限性
J Org Chem. 2009 Jan 2;74(1):182-7. doi: 10.1021/jo801644s.
6
Rh-catalyzed (5+2) cycloadditions of 3-acyloxy-1,4-enynes and alkynes: computational study of mechanism, reactivity, and regioselectivity.铑催化的 3-酰氧基-1,4-烯炔和炔烃的 (5+2) 环加成反应：机理、反应性和区域选择性的计算研究。
J Am Chem Soc. 2013 Jun 26;135(25):9271-4. doi: 10.1021/ja4036785. Epub 2013 Jun 14.
7
Rhodium-catalyzed oxidative coupling of triarylmethanols with internal alkynes via successive C-H and C-C bond cleavages.铑催化的三芳基甲醇与内炔烃通过连续的C-H和C-C键裂解进行氧化偶联反应。
J Org Chem. 2008 Jan 4;73(1):298-300. doi: 10.1021/jo7022087. Epub 2007 Dec 5.
8
Easy access to isoquinolines and tetrahydroquinolines from ketoximes and alkynes via rhodium-catalyzed C-H bond activation.通过铑催化的 C-H 键活化，从酮肟和炔烃中轻松获得异喹啉和四氢喹啉。
J Org Chem. 2009 Dec 18;74(24):9359-64. doi: 10.1021/jo902084j.
9
Rhodium-catalyzed direct coupling of biaryl pyridine derivatives with internal alkynes.铑催化的联芳基吡啶衍生物与内炔的直接偶联反应。
Chem Commun (Camb). 2014 Aug 4;50(60):8204-7. doi: 10.1039/c4cc02822h.
10
Ruthenium-catalyzed synthesis of isoquinolones with 8-aminoquinoline as a bidentate directing group in C-H functionalization.钌催化的 8-氨基喹啉作为双齿导向基团在 C-H 功能化中的异喹啉合成。
J Org Chem. 2014 May 2;79(9):3963-72. doi: 10.1021/jo500424p. Epub 2014 Apr 23.
引用本文的文献
1
Design and synthesis of novel 4-aryl-2-benzoyl-imidazoles as colchicine binding site inhibitors.新型4-芳基-2-苯甲酰基咪唑作为秋水仙碱结合位点抑制剂的设计与合成
Eur J Med Chem. 2025 Nov 15;298:118021. doi: 10.1016/j.ejmech.2025.118021. Epub 2025 Aug 4.
2
Organocatalytic Electrophilic Arene Amination: Rapid Synthesis of 2-Quinolones.有机催化亲电芳烃胺化反应：2-喹诺酮类的快速合成
Chemistry. 2025 Jan 27;31(6):e202403524. doi: 10.1002/chem.202403524. Epub 2024 Nov 27.
3
Merging the Norrish type I reaction and transition metal catalysis: photo- and Rh-promoted borylation of C-C σ-bonds of aryl ketones.Norrish I型反应与过渡金属催化的融合：光促进和铑促进的芳基酮C-C σ键硼化反应
Chem Sci. 2023 Jan 26;14(8):1960-1965. doi: 10.1039/d2sc06801j. eCollection 2023 Feb 22.
4
Nickel-catalyzed skeletal transformation of tropone derivatives C-C bond activation: catalyst-controlled access to diverse ring systems.镍催化的环庚三烯酮衍生物的骨架转化：C-C键活化——催化剂控制的多种环系合成方法
Chem Sci. 2022 Apr 4;13(17):4922-4929. doi: 10.1039/d2sc01394k. eCollection 2022 May 4.
5
Catalytic Net Oxidative C-C Activation and Silylation of Cyclopropanols with a Traceless Acetal Directing Group.带有无痕缩醛导向基团的环丙醇的催化净氧化碳-碳活化和硅烷化反应
ACS Catal. 2022 Feb 4;12(3):1764-1774. doi: 10.1021/acscatal.1c04628. Epub 2022 Jan 18.
6
One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(iii)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor.通过铑（III）催化未保护的芳基酰胺与3-重氮喹啉二酮的环化反应一锅法构建多样且功能化的异色满并喹啉二酮及其在荧光传感器中的应用
RSC Adv. 2019 Jun 3;9(30):17347-17357. doi: 10.1039/c9ra03146d. eCollection 2019 May 29.
7
One-pot copper-catalyzed three-component reaction: a modular approach to functionalized 2-quinolones.一锅法铜催化三组分反应：一种合成功能化2-喹诺酮的模块化方法。
RSC Adv. 2020 Feb 24;10(13):7855-7866. doi: 10.1039/d0ra01352h. eCollection 2020 Feb 18.
8
Cobalt-catalyzed intramolecular decarbonylative coupling of acylindoles and diarylketones through the cleavage of C-C bonds.钴催化通过碳-碳键断裂实现的酰基吲哚与二芳基酮的分子内脱羰偶联反应。
Chem Sci. 2020 Oct 16;11(45):12336-12340. doi: 10.1039/d0sc04326e.
9
Recent Advances in One-Pot Modular Synthesis of 2-Quinolones.一锅法模块化合成 2-喹诺酮的最新进展。
Molecules. 2020 Nov 20;25(22):5450. doi: 10.3390/molecules25225450.
10
Green Synthesis of Substituted Anilines and Quinazolines from Isatoic Anhydride-8-amide.靛红酸酐-8-酰胺的取代苯胺和喹唑啉的绿色合成。
Sci Rep. 2019 Oct 3;9(1):14258. doi: 10.1038/s41598-019-50776-y.
本文引用的文献
1
Direct activation of relatively unstrained carbon-carbon bonds in homogeneous systems.均相体系中相对无张力碳-碳键的直接活化
Org Chem Front. 2014 Jul 1;1(5):567-581. doi: 10.1039/c4qo00053f. Epub 2014 Mar 27.
2
Metal Insertion into C-C Bonds in Solution.溶液中碳-碳键的金属插入反应
Angew Chem Int Ed Engl. 1999 Apr 1;38(7):870-883. doi: 10.1002/(SICI)1521-3773(19990401)38:7<870::AID-ANIE870>3.0.CO;2-3.
3
Nickel-catalyzed reaction of thioisatins and alkynes: a facile synthesis of thiochromones.镍催化硫代异氰酸酯与炔烃的反应：硫色酮的简便合成方法。
Org Lett. 2014 Nov 7;16(21):5660-2. doi: 10.1021/ol5026102. Epub 2014 Oct 27.
4
Divergent syntheses of fused β-naphthol and indene scaffolds by rhodium-catalyzed direct and decarbonylative alkyne-benzocyclobutenone couplings.铑催化的直接和脱羰炔烃-苯并环丁烯酮偶联反应合成稠合 β-萘酚和茚基骨架的不同方法。
Angew Chem Int Ed Engl. 2014 Feb 3;53(6):1674-8. doi: 10.1002/anie.201310100. Epub 2014 Jan 21.
5
Pd(II)-catalyzed phosphorylation of aryl C-H bonds.钯（II）催化的芳基 C-H 键磷酸化反应。
J Am Chem Soc. 2013 Jun 26;135(25):9322-5. doi: 10.1021/ja404526x. Epub 2013 Jun 17.
6
Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones.导向基团增强了氨基取代的环丙烷的羰基环化反应：铑催化的 N-杂双环烯酮的多组分合成。
J Am Chem Soc. 2013 Apr 3;135(13):4992-5. doi: 10.1021/ja401936c. Epub 2013 Mar 22.
7
[5 + 2] cycloaddition reactions in organic and natural product synthesis.有机合成和天然产物合成中的[5 + 2]环加成反应
Chem Rev. 2013 Mar 13;113(3):2244-66. doi: 10.1021/cr300087g. Epub 2012 Nov 15.
8
Rhodium-catalyzed ring opening of benzocyclobutenols with site-selectivity complementary to thermal ring opening.铑催化的苯并环丁烯醇的开环反应，具有与热开环互补的位点选择性。
J Am Chem Soc. 2012 Oct 24;134(42):17502-4. doi: 10.1021/ja309013a. Epub 2012 Oct 11.
9
Extrusion of CO from aryl ketones: rhodium(I)-catalyzed C-C bond cleavage directed by a pyridine group.芳基酮中 CO 的挤出：由吡啶基团导向的铑（I）催化的 C-C 键断裂。
Angew Chem Int Ed Engl. 2012 Mar 12;51(11):2690-4. doi: 10.1002/anie.201107136. Epub 2012 Feb 6.
10
Rhodium catalyzed chelation-assisted C-H bond functionalization reactions.铑催化的螯合辅助 C-H 键功能化反应。
Acc Chem Res. 2012 Jun 19;45(6):814-25. doi: 10.1021/ar200190g. Epub 2011 Dec 8.
Zotero 插件