利用硝基芳烃自由基阴离子的反应活性通过电化学还原环化制备喹啉 N-氧化物。
Harnessing the Reactivity of Nitroarene Radical Anions to Create Quinoline N-Oxides by Electrochemical Reductive Cyclization.
作者信息
Zhu Haoran, Powell Jair N, Geldchen Victoria A, Drumheller Adam S, Driver Tom G
机构信息
Department of Chemistry, University of Illinois Chicago 845 West Taylor Street, Chicago, 60607, Illinois, USA.
出版信息
Angew Chem Int Ed Engl. 2025 Jan 21;64(4):e202416126. doi: 10.1002/anie.202416126. Epub 2024 Nov 16.
Abstract
Electrochemical reduction of 2-allyl-substituted nitroarenes using a simple, undivided electrochemical cell with non-precious electrodes to generate nitroarene radical anions was developed. The nitroarene radical anion intermediates participate in 1,5-hydrogen atom transfer reactions to construct quinoline N-oxides bearing aryl-, heteroaryl-, alkenyl-, benzyl-, sulfonyl-, or carboxyl groups.
摘要
利用一个带有非贵金属电极的简单、无隔膜电化学池对2-烯丙基取代的硝基芳烃进行电化学还原，以生成硝基芳烃自由基阴离子。硝基芳烃自由基阴离子中间体参与1,5-氢原子转移反应，构建带有芳基、杂芳基、烯基、苄基、磺酰基或羧基的喹啉N-氧化物。
相似文献
1
Harnessing the Reactivity of Nitroarene Radical Anions to Create Quinoline N-Oxides by Electrochemical Reductive Cyclization.利用硝基芳烃自由基阴离子的反应活性通过电化学还原环化制备喹啉 N-氧化物。
Angew Chem Int Ed Engl. 2025 Jan 21;64(4):e202416126. doi: 10.1002/anie.202416126. Epub 2024 Nov 16.
2
Direct Electrochemical Synthesis of 2,3-Disubstituted Quinoline N-oxides by Cathodic Reduction of Nitro Arenes.通过硝基芳烃的阴极还原直接电化学合成2,3-二取代喹啉N-氧化物
Chemistry. 2023 Feb 24;29(12):e202203319. doi: 10.1002/chem.202203319. Epub 2023 Jan 16.
3
Regioselective bond cleavage in the dissociative electron transfer to benzyl thiocyanates: the role of radical/ion pair formation.苄基硫氰酸酯离解电子转移中的区域选择性键断裂：自由基/离子对形成的作用。
J Am Chem Soc. 2006 May 24;128(20):6595-604. doi: 10.1021/ja056730u.
4
Progress in the Electrochemical Reactions of Sulfonyl Compounds.磺酰化合物电化学反应的研究进展。
ChemSusChem. 2022 Apr 7;15(7):e202102557. doi: 10.1002/cssc.202102557. Epub 2022 Feb 24.
5
Simple and scalable electrochemical synthesis of 2,1-benzisoxazoles and quinoline N-oxides.简单且可扩展的 2,1-苯并异恶唑和喹啉 N-氧化物的电化学合成。
Chem Commun (Camb). 2019 Oct 8;55(81):12255-12258. doi: 10.1039/c9cc06054e.
6
SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles.通过 2-氮杂丙烯负离子来实现硝芳烃的 SET 活化，从而直接得到 2,5-二氢-1,2,4-噁二唑。
Nat Commun. 2021 Dec 3;12(1):7060. doi: 10.1038/s41467-021-26767-x.
7
Chemistry with Electrochemically Generated N-Centered Radicals.电化学产生的氮中心自由基化学
Acc Chem Res. 2019 Dec 17;52(12):3339-3350. doi: 10.1021/acs.accounts.9b00472. Epub 2019 Nov 27.
8
Reductive Arylation of Nitroarenes with Chloroarenes: Reducing Conditions Enable New Reactivity from Palladium Catalysts.硝基芳烃与氯代芳烃的还原芳基化反应：还原条件赋予钯催化剂新的反应活性。
J Am Chem Soc. 2023 Jul 26;145(29):16150-16159. doi: 10.1021/jacs.3c04647. Epub 2023 Jul 12.
9
Synthesis of indoles by intermolecular cyclization of unfunctionalized nitroarenes and alkynes, catalyzed by palladium-phenanthroline complexes.钯-菲咯啉配合物催化未官能化硝基芳烃与炔烃的分子间环化反应合成吲哚。
J Org Chem. 2006 May 12;71(10):3748-53. doi: 10.1021/jo060073m.
10
Anaerobic Hydroxylation of C(sp)-H Bonds Enabled by the Synergistic Nature of Photoexcited Nitroarenes.偕同激发态硝基芳烃的协同作用实现 C(sp)-H 键的厌氧羟化
J Am Chem Soc. 2023 Feb 8;145(5):2794-2799. doi: 10.1021/jacs.2c13502. Epub 2023 Jan 25.
本文引用的文献
1
Recent Advances to Mediate Reductive Processes of Nitroarenes Using Single-Electron Transfer, Organomagnesium, or Organozinc Reagents.利用单电子转移、有机镁或有机锌试剂介导硝基芳烃还原过程的最新进展。
Synthesis (Stuttg). 2022 Jul;54(14):3142-3161. doi: 10.1055/a-1792-6579. Epub 2022 May 30.
2
The Development and Mechanistic Study of an Iron-Catalyzed Intramolecular Nitroso Ene Reaction of Nitroarenes.铁催化硝基芳烃分子内亚硝基烯反应的发展与机理研究
ACS Catal. 2023 Nov 17;13(22):15175-15181. doi: 10.1021/acscatal.3c04483. Epub 2023 Nov 8.
3
Nitroarenes and nitroalkenes as potential amino sources for the synthesis of N-heterocycles.作为合成氮杂环潜在氨基来源的硝基芳烃和硝基烯烃。
Org Biomol Chem. 2023 Mar 15;21(11):2254-2271. doi: 10.1039/d3ob00064h.
4
Chemoselective Primary Amination of Aryl Boronic Acids by P/P═O-Catalysis: Synthetic Capture of the Transient Nef Intermediate HNO.通过 P/P═O 催化的芳基硼酸的化学选择性伯胺化反应：瞬态 Nef 中间体 HNO 的合成捕获。
J Am Chem Soc. 2022 May 25;144(20):8902-8907. doi: 10.1021/jacs.2c02922. Epub 2022 May 12.
5
Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds.杂环纳米石墨烯和其他多环杂芳烃化合物的最新进展。
Chem Rev. 2022 Jan 12;122(1):565-788. doi: 10.1021/acs.chemrev.1c00449. Epub 2021 Dec 1.
6
Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids.电化学还原芳基硼酸对硝基芳烃的芳基化反应。
ChemSusChem. 2021 Dec 17;14(24):5399-5404. doi: 10.1002/cssc.202101924. Epub 2021 Oct 18.
7
Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.反离子调控叔丁氧基金属介导的单电子转移到硝代亚苄基构建 N-羟基吲哚或氧化吲哚。
Angew Chem Int Ed Engl. 2021 Aug 23;60(35):19207-19213. doi: 10.1002/anie.202104319. Epub 2021 Jul 20.
8
C-H functionalization reactions enabled by hydrogen atom transfer to carbon-centered radicals.通过氢原子转移到碳中心自由基实现的C-H官能团化反应。
Chem Sci. 2020 Nov 16;11(48):12974-12993. doi: 10.1039/d0sc04881j.
9
Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes.铁催化硝基芳烃参与的烯烃的厌氧 Mukaiyama 型水合反应。
Angew Chem Int Ed Engl. 2021 Apr 6;60(15):8313-8320. doi: 10.1002/anie.202015740. Epub 2021 Mar 3.
10
NH-HO Enabled Umpolung Cyclization of -Nitro Chalcones for the Construction of Quinoline -Oxides.NH-HO实现的用于构建喹啉-氧化物的对硝基查尔酮的极性翻转环化反应。
Org Lett. 2021 Jan 15;23(2):595-600. doi: 10.1021/acs.orglett.0c04162. Epub 2020 Dec 30.
Zotero 插件