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光氧化还原介导的自由基共轭加成反应的最新进展：吉泽反应的扩展工具包

Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

作者信息

Gant Kanegusuku Anastasia L, Roizen Jennifer L

机构信息

Department of Chemistry, Duke University, Box 90346, Durham, NC, 27708-0354, USA.

出版信息

Angew Chem Int Ed Engl. 2021 Sep 20;60(39):21116-21149. doi: 10.1002/anie.202016666. Epub 2021 Jul 21.

DOI:10.1002/anie.202016666
PMID:33629454
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8382814/
Abstract

Photomediated Giese reactions are at the forefront of radical chemistry, much like the classical tin-mediated Giese reactions were nearly forty years ago. With the global recognition of organometallic photocatalysts for the mild and tunable generation of carbon-centered radicals, chemists have developed a torrent of strategies to form previously inaccessible radical intermediates that are capable of engaging in intermolecular conjugate addition reactions. This Review summarizes advances in photoredox-mediated Giese reactions since 2013, with a focus on the breadth of methods that provide access to crucial carbon-centered radical intermediates that can engage in radical conjugate addition processes.

摘要

光介导的吉泽反应处于自由基化学的前沿，就像近四十年前经典的锡介导的吉泽反应一样。随着有机金属光催化剂在温和且可调控地生成碳中心自由基方面得到全球认可，化学家们已经开发出大量策略来形成以前难以获得的自由基中间体，这些中间体能够进行分子间共轭加成反应。本综述总结了自2013年以来光氧化还原介导的吉泽反应的进展，重点关注提供获取能够参与自由基共轭加成过程的关键碳中心自由基中间体的方法的广度。

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3
Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.利用含氮自由基修饰C-H官能化反应中的位置选择性：1,6-氢原子转移过程的通用方法
J Org Chem. 2025 Aug 1;90(30):10786-10796. doi: 10.1021/acs.joc.5c01157. Epub 2025 Jul 21.
4
Synthesis of polysubstituted cyclobutanes through a photoredox strain-release/[3,3]-rearrangement cascade.通过光氧化还原应变释放/[3,3]-重排级联反应合成多取代环丁烷
Chem Sci. 2025 May 14. doi: 10.1039/d5sc01431j.
5
Kharasch-Type Haloalkylation of Alkenes by Photoinduced Copper Catalysis.光诱导铜催化烯烃的卡拉施型卤烷基化反应
J Am Chem Soc. 2025 Jun 4;147(22):18438-18444. doi: 10.1021/jacs.5c05699. Epub 2025 May 20.
6
Preassembly-Controlled Radical Recombination at Bismuth: Decarboxylative C─N Coupling with Sulfonamides.铋催化的预组装控制自由基重组反应：与磺酰胺的脱羧C─N偶联反应
Chemistry. 2025 May 19;31(28):e202500396. doi: 10.1002/chem.202500396. Epub 2025 Apr 21.
7
Photocatalytic Generation of a Ground-State Electron Donor Through Water Activation.通过水活化光催化生成基态电子供体。
Angew Chem Int Ed Engl. 2025 Jun 2;64(23):e202501757. doi: 10.1002/anie.202501757. Epub 2025 Apr 26.
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Visible-Light Photocatalysis for Sustainable Chromene Synthesis and Functionalization.用于可持续色烯合成与功能化的可见光光催化
Chemistry. 2025 May 22;31(29):e202500283. doi: 10.1002/chem.202500283. Epub 2025 Apr 3.
9
Unified Hydrogen Atom Transfer Approach To Construct Vicinal Functionality.构建邻位官能团的统一氢原子转移方法。
Org Lett. 2025 May 2;27(17):4417-4422. doi: 10.1021/acs.orglett.4c04767. Epub 2025 Feb 6.
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Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study.吖啶/路易斯酸配合物作为高效光催化剂：实验与机理的联合研究
ACS Catal. 2024 Oct 4;14(19):14574-14585. doi: 10.1021/acscatal.4c04897. Epub 2024 Sep 16.
Synlett. 2020 Jan;31(2):102-116. doi: 10.1055/s-0039-1691501. Epub 2019 Nov 27.
4
A droplet microfluidic platform for high-throughput photochemical reaction discovery.一种用于高通量光化学生成发现的液滴微流控平台。
Nat Commun. 2020 Dec 3;11(1):6202. doi: 10.1038/s41467-020-19926-z.
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Photo-Mediated Decarboxylative Giese-Type Reaction Using Organic Pyrimidopteridine Photoredox Catalysts.使用有机嘧啶蝶啶光氧化还原催化剂的光介导脱羧基吉斯型反应
J Org Chem. 2020 Nov 6;85(21):13853-13867. doi: 10.1021/acs.joc.0c01955. Epub 2020 Oct 9.
6
Stereoselective and Divergent Construction of β-Thiolated/Selenolated Amino Acids via Photoredox-Catalyzed Asymmetric Giese Reaction.通过光氧化还原催化不对称 Giese 反应立体选择性和多样化构建β-硫代/硒代氨基酸。
J Am Chem Soc. 2020 Aug 19;142(33):14201-14209. doi: 10.1021/jacs.0c04994. Epub 2020 Aug 10.
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C(sp)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow.使用多钨酸盐光催化在流动相中对轻烃进行 C(sp)-H 官能化。
Science. 2020 Jul 3;369(6499):92-96. doi: 10.1126/science.abb4688.
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Remote C-C bond formation via visible light photoredox-catalyzed intramolecular hydrogen atom transfer.通过可见光光氧化还原催化的分子内氢原子转移实现远程碳-碳键的形成。
Org Biomol Chem. 2020 Jun 24;18(24):4519-4532. doi: 10.1039/d0ob00854k.
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Cerium-Catalyzed C-H Functionalizations of Alkanes Utilizing Alcohols as Hydrogen Atom Transfer Agents.铈催化的烷烃 C-H 功能化反应：醇作为氢原子转移试剂的应用。
J Am Chem Soc. 2020 Apr 1;142(13):6216-6226. doi: 10.1021/jacs.0c00212. Epub 2020 Mar 23.
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N-Centered Radical Directed Remote C-H Bond Functionalization via Hydrogen Atom Transfer.N 中心自由基导向远程 C-H 键功能化反应通过氢原子转移实现。
Chem Asian J. 2020 Mar 16;15(6):651-672. doi: 10.1002/asia.201901744. Epub 2020 Feb 18.