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通过电还原自由基加成-极性环化串联反应合成环烷烃

Electroreductive Radical Addition-Polar Cyclization Cascade to Access Cycloalkanes.

作者信息

Wang Yi, Deng Jiachen, Ressler Andrew J, Lin Song

机构信息

Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.

出版信息

Org Lett. 2024 Jan 12;26(1):116-121. doi: 10.1021/acs.orglett.3c03722. Epub 2023 Dec 29.

DOI:10.1021/acs.orglett.3c03722
PMID:38157449
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11192528/
Abstract

Compared with flat aromatic scaffolds, three-dimensional aliphatic ring systems feature high structural complexity and topological diversity and, thus, have received increasing attention in drug discovery. Herein, we describe a mild and general electrochemical method for the modular synthesis of structurally distinct cyclic compounds, including monocyclic alkanes, benzo-fused ring systems, and spirocycles, from readily available alkenes and alkyl halides via a radical-polar crossover mechanism.

摘要

与平面芳香骨架相比,三维脂肪族环系统具有高度的结构复杂性和拓扑多样性,因此在药物发现中受到越来越多的关注。在此,我们描述了一种温和且通用的电化学方法,用于通过自由基-极性交叉机制从易得的烯烃和卤代烃模块化合成结构各异的环状化合物,包括单环烷烃、苯并稠环系统和螺环化合物。

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本文引用的文献

1
Deep Electroreductive Chemistry: Harnessing Carbon- and Silicon-based Reactive Intermediates in Organic Synthesis.深度电还原化学:在有机合成中利用碳基和硅基反应中间体
ACS Catal. 2023 Jun 16;13(12):8038-8048. doi: 10.1021/acscatal.3c01174. Epub 2023 May 31.
2
Three-Component Cross-Electrophile Coupling: Regioselective Electrochemical Dialkylation of Alkenes.三组分交叉亲电试剂偶联反应:烯烃的区域选择性电化学二烷基化反应
J Am Chem Soc. 2023 Oct 18;145(41):22298-22304. doi: 10.1021/jacs.3c06794. Epub 2023 Oct 6.
3
Electrochemically Driven Deoxygenative Borylation of Alcohols and Carbonyl Compounds.
醇类和羰基化合物的电化学驱动脱氧硼化反应
J Am Chem Soc. 2023 Aug 9;145(31):16966-16972. doi: 10.1021/jacs.3c03418. Epub 2023 Jul 27.
4
Electroreductive Cross-Electrophile Coupling (eXEC) Reactions.电还原交叉亲电试剂偶联(eXEC)反应
Angew Chem Int Ed Engl. 2023 Nov 6;62(45):e202306679. doi: 10.1002/anie.202306679. Epub 2023 Jul 12.
5
An Electrochemical Strategy to Synthesize Disilanes and Oligosilanes from Chlorosilanes.电化学策略合成氯硅烷中的二硅烷和低聚硅烷。
Angew Chem Int Ed Engl. 2023 Jun 26;62(26):e202303592. doi: 10.1002/anie.202303592. Epub 2023 May 15.
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Access to functionalized alkynylcyclopropanes reductive radical-polar crossover-based reactions of 1,3-enynes with alkyl radicals.获得官能化炔基环丙烷 1,3-烯炔与烷基自由基的基于还原自由基-极性交叉的反应。
Org Biomol Chem. 2023 Jan 25;21(4):732-737. doi: 10.1039/d2ob02155b.
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Nat Prod Rep. 2022 Aug 17;39(8):1544-1556. doi: 10.1039/d2np00001f.
8
Electrochemically driven cross-electrophile coupling of alkyl halides.电化学驱动的卤代烷烃的交叉亲电偶联。
Nature. 2022 Apr;604(7905):292-297. doi: 10.1038/s41586-022-04540-4. Epub 2022 Feb 21.
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Arylcyclopropane yet in its infancy: the challenges and recent advances in its functionalization.芳基环丙烷尚处于起步阶段:其功能化的挑战和最新进展。
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