喹啉与烯烃的光致非芳构化环加成反应：范围和机理研究。
Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies.
机构信息
Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, Indiana47405, United States.
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 36, 48149Münster, Germany.
出版信息
J Am Chem Soc. 2022 Sep 28;144(38):17680-17691. doi: 10.1021/jacs.2c07726. Epub 2022 Sep 15.
Abstract
Photochemical dearomative cycloaddition has emerged as a useful strategy to rapidly generate molecular complexity. Within this context, stereo- and regiocontrolled intermolecular -cycloadditions are rare. Herein, a method to achieve photochemical cycloaddition of quinolines and alkenes is shown. Emphasis is placed on generating sterically congested products and reaction of highly substituted alkenes and allenes. In addition, the mechanistic details of the process are studied, which revealed a reversible radical addition and a selectivity-determining radical recombination. The regio- and stereochemical outcome of the reaction is also rationalized.
摘要
光致非芳构化环加成已成为快速生成分子复杂性的有用策略。在这种情况下，立体和区域控制的分子间环加成很少见。本文展示了一种实现喹啉和烯烃光化学环加成的方法。重点是生成空间拥挤的产物，以及高取代烯烃和丙二烯的反应。此外，还研究了该过程的机理细节，揭示了可逆的自由基加成和选择性决定的自由基重组。反应的区域和立体化学结果也得到了合理的解释。
相似文献
1
Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies.喹啉与烯烃的光致非芳构化环加成反应：范围和机理研究。
J Am Chem Soc. 2022 Sep 28;144(38):17680-17691. doi: 10.1021/jacs.2c07726. Epub 2022 Sep 15.
2
Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes.双环氮杂芳烃与烯烃的光致分子间去芳构化环加成反应。
Science. 2021 Mar 26;371(6536):1338-1345. doi: 10.1126/science.abg0720. Epub 2021 Mar 25.
3
Synthesis of complex bicyclic scaffolds by intermolecular photosensitized dearomative cycloadditions of activated alkenes and naphthalenes.通过活化烯烃与萘的分子间光敏去芳构化环加成反应合成复杂双环骨架
Chem Sci. 2022 Oct 14;13(45):13582-13587. doi: 10.1039/d2sc04789f. eCollection 2022 Nov 23.
4
ORGANIC CHEMISTRY. Iron-catalyzed intermolecular [2+2] cycloadditions of unactivated alkenes.有机化学。铁催化的非活化烯烃的分子间[2+2]环加成反应。
Science. 2015 Aug 28;349(6251):960-3. doi: 10.1126/science.aac7440.
5
Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes.分子内手性转移[2+2]环加成反应：丙二烯酸酯和烯烃的反应
Org Lett. 2017 Jul 21;19(14):3703-3706. doi: 10.1021/acs.orglett.7b01420. Epub 2017 Jul 7.
6
Lewis acids promoted formal intramolecular [3 + 2] parallel and cross-cycloadditions of cyclopropane 1,1-diesters with allenes.路易斯酸促进了环丙烷 1,1-二酯与丙二烯的分子内[3+2]平行和交叉环加成反应。
Org Lett. 2013 Nov 15;15(22):5682-5. doi: 10.1021/ol402662j. Epub 2013 Oct 30.
7
Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes.自由基氧化还原接力催化：N-酰基氮丙啶与烯烃的[3+2]环加成反应。
J Am Chem Soc. 2017 Sep 6;139(35):12141-12144. doi: 10.1021/jacs.7b06723. Epub 2017 Aug 25.
8
Mechanistic studies of UV assisted [4 + 2] cycloadditions in synthetic efforts toward vibsanin E.在合成 vibsanin E 的过程中，紫外线辅助 [4 + 2] 环加成反应的机理研究。
J Am Chem Soc. 2007 Sep 5;129(35):10763-72. doi: 10.1021/ja072090e. Epub 2007 Aug 11.
9
Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes.桥连1,3-二氮杂环庚烷的去芳构化光催化构建
Angew Chem Int Ed Engl. 2020 Mar 2;59(10):4121-4130. doi: 10.1002/anie.201914390. Epub 2020 Jan 27.
10
How torsional effects cause attack at sterically crowded concave faces of bicyclic alkenes.扭转效应如何导致双环烯烃在空间拥挤的凹面发生反应。
J Org Chem. 2014 Sep 5;79(17):8304-12. doi: 10.1021/jo501557z. Epub 2014 Aug 21.
引用本文的文献
1
Photoredox catalytic asymmetric dearomative [3 + 2] cycloaddition of isoquinolines with enones.异喹啉与烯酮的光氧化还原催化不对称脱芳构化[3+2]环加成反应
Nat Commun. 2025 Aug 13;16(1):7520. doi: 10.1038/s41467-025-62876-7.
2
London Dispersion as a Design Element in Molecular Catalysis.伦敦色散力作为分子催化中的一个设计元素。
J Am Chem Soc. 2025 Aug 20;147(33):29611-29623. doi: 10.1021/jacs.5c09212. Epub 2025 Aug 11.
3
Visible light-mediated dearomative spirocyclization/imination of nonactivated arenes through energy transfer catalysis.通过能量转移催化实现可见光介导的未活化芳烃的去芳构化螺环化/亚胺化反应
Nat Commun. 2025 Apr 16;16(1):3610. doi: 10.1038/s41467-025-58808-0.
4
Photocatalytic Hydrogenation of Quinolines to Form 1,2,3,4-Tetrahdyroquinolines Using Water as the Hydrogen Atom Donor.以水作为氢原子供体将喹啉光催化加氢生成1,2,3,4-四氢喹啉
Angew Chem Int Ed Engl. 2025 Jun 17;64(25):e202502864. doi: 10.1002/anie.202502864. Epub 2025 May 8.
5
Visible light-driven dearomative meta-cycloadditions of 2-acetonaphthalenes via triplet energy transfer cascade.通过三重态能量转移级联实现的2-乙酰萘的可见光驱动去芳构化间环加成反应
Nat Commun. 2025 Mar 27;16(1):2991. doi: 10.1038/s41467-025-58285-5.
6
Ligand-Controlled Regioselective Dearomative Vicinal and Conjugate Hydroboration of Quinolines.喹啉的配体控制区域选择性去芳构化邻位和共轭硼氢化反应
J Am Chem Soc. 2025 Apr 9;147(14):11906-11914. doi: 10.1021/jacs.4c17247. Epub 2025 Mar 27.
7
Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.重新构想脱芳构化：亲芳烃介导的单原子插入和π扩展。
Acc Chem Res. 2025 Apr 1;58(7):1134-1150. doi: 10.1021/acs.accounts.5c00035. Epub 2025 Mar 11.
8
Boron Enabled Directed [2+2]- and Dearomative [4+2]-Cycloadditions Initiated by Energy Transfer.硼促进的由能量转移引发的定向[2+2]环加成反应和脱芳构化[4+2]环加成反应。
Angew Chem Int Ed Engl. 2025 Jan 21;64(4):e202416215. doi: 10.1002/anie.202416215. Epub 2024 Nov 7.
9
Direct photochemical intramolecular [4 + 2] cycloadditions of dehydrosecodine-type substrates for the synthesis of the -type scaffold and divergent [2 + 2] cycloadditions employing micro-flow system.用于合成 - 型支架的脱氢二氢可待因型底物的直接光化学分子内[4 + 2]环加成反应以及采用微流系统的发散性[2 + 2]环加成反应。
Chem Sci. 2024 Sep 25;15(38):15599-609. doi: 10.1039/d4sc02597k.
10
Visible light-induced chemoselective 1,2-diheteroarylation of alkenes.可见光诱导的烯烃的化学选择性1,2-二杂芳基化反应
Nat Commun. 2024 Jul 19;15(1):6102. doi: 10.1038/s41467-024-50460-4.
本文引用的文献
1
Visible-Light Photocatalyzed -(3 + 2) Cycloadditions of Quinolines.可见光促进的喹啉的[3+2]环加成反应。
J Am Chem Soc. 2022 Aug 31;144(34):15662-15671. doi: 10.1021/jacs.2c05687. Epub 2022 Aug 19.
2
Visible Light-Mediated Dearomative Hydrogen Atom Abstraction/ Cyclization Cascade of Indoles.可见光促进吲哚的去芳构化氢原子摘取/环化级联反应。
Angew Chem Int Ed Engl. 2022 Apr 25;61(18):e202200555. doi: 10.1002/anie.202200555. Epub 2022 Mar 7.
3
Visible-light induced dearomatization reactions.可见光诱导去芳构化反应。
Chem Soc Rev. 2022 Mar 21;51(6):2145-2170. doi: 10.1039/c9cs00311h.
4
Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug Design.苯环的生物电子等排体：在先导化合物优化和药物设计中的近期策略性应用
J Med Chem. 2021 Oct 14;64(19):14046-14128. doi: 10.1021/acs.jmedchem.1c01215. Epub 2021 Sep 30.
5
Visible-Light-Induced Dearomatization of Indoles/Pyrroles with Vinylcyclopropanes: Expedient Synthesis of Structurally Diverse Polycyclic Indolines/Pyrrolines.可见光诱导吲哚/吡咯与乙烯基环丙烷的去芳构化反应：构建结构多样的多环吲哚/吡咯啉的便捷方法。
J Am Chem Soc. 2021 Aug 25;143(33):13441-13449. doi: 10.1021/jacs.1c07082. Epub 2021 Aug 16.
6
Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins.质子化增强的三重态反应性在喹啉与烯烃的去芳构化光环加成中的应用。
Org Lett. 2021 Aug 20;23(16):6257-6261. doi: 10.1021/acs.orglett.1c02026. Epub 2021 Jul 29.
7
Enantioselective Photochemical Reactions Enabled by Triplet Energy Transfer.由三重态能量转移实现的对映选择性光化学反应。
Chem Rev. 2022 Jan 26;122(2):1626-1653. doi: 10.1021/acs.chemrev.1c00272. Epub 2021 Jul 6.
8
Isotope Effects and the Mechanism of Photoredox-Promoted [2 + 2] Cycloadditions of Enones.同位素效应与光氧化还原促进烯酮[2 + 2]环加成反应的机理。
J Org Chem. 2021 May 7;86(9):6305-6313. doi: 10.1021/acs.joc.1c00099. Epub 2021 Apr 23.
9
Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes.双环氮杂芳烃与烯烃的光致分子间去芳构化环加成反应。
Science. 2021 Mar 26;371(6536):1338-1345. doi: 10.1126/science.abg0720. Epub 2021 Mar 25.
10
Visible-Light-Induced Intramolecular Double Dearomative Cycloaddition of Arenes.可见光诱导的芳烃分子内双去芳构化环加成反应
Angew Chem Int Ed Engl. 2021 Mar 22;60(13):7036-7040. doi: 10.1002/anie.202016899. Epub 2021 Feb 24.
Zotero 插件