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Electrosynthesis of Stabilized Diazo Compounds from Hydrazones

Cite this: Org. Lett. 2022, 24, 25, 4665–4669
Publication Date (Web):June 21, 2022
https://doi.org/10.1021/acs.orglett.2c01803
Copyright © 2022 American Chemical Society

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    Abstract

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    An electrochemical synthesis of diazo compounds from hydrazones in yields as high as 99% was performed. This method was elaborated as a useful synthetic method and demonstrated on various diazo compounds (24 examples). Apart from exhibiting an efficiency that matched that of commonly used harsh and toxic chemical oxidants, this reaction is practically simple to set up, requires mild conditions, and is highly electron efficient (3 F/mol).

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.2c01803.

    • Experimental procedures, characterization data of starting material and target compounds, and copies of 1H, 13C, and 19F NMR spectra (PDF)

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    Cited By

    This article is cited by 7 publications.

    1. Zhicheng Xiong, Hongsheng Nie, Shuai Zhang, Meiqian Hu, Changsheng Qin, Shoucai Wang, Fanghua Ji, Guangbin Jiang. Electrochemically Driven Selective Removal of the S═N Bond-Directing Group Using Cyclohexanone Oxime as the Mediator. The Journal of Organic Chemistry 2023, 88 (7) , 4334-4344. https://doi.org/10.1021/acs.joc.2c02940
    2. Martin Breugst, Jennifer N. Andexer, Sebastian B. Beil, Rolf Breinbauer, Oliver Dumele, Martin Ernst, Urs Gellrich, Philipp Germer, Michael Giese, Tobias A. M. Gulder, Peter Huy, Wolfgang Hüttel, Stephanie Kath‐Schorr, Karsten Körber, Markus Kordes, Christian Kuttruff, Thomas Lindel, Robin Meier, Sebastian Myllek, Norbert Schaschke, Fabian Pfrengle, Jörg Pietruszka, Hanna Sebode, Mathias O. Senge, Golo Storch, Bernd F. Straub, Johannes Teichert, Siegfried R. Waldvogel, Thomas Werner, Christian Winter. Trendbericht Organische Chemie 2023. Nachrichten aus der Chemie 2023, 71 (3) , 40-66. https://doi.org/10.1002/nadc.20234135542
    3. Yi Lu, Zhirui Liu, Chao Liu, Yunpeng Wu, Lu Li, Siyuan Liu, Hong Wang, Wei Gao, Zhenxian Liu, Jianbin Chen. Transition metal-free electrochemical fluorotrifluoromethylation of Styrenes. Organic Chemistry Frontiers 2023, 10 (5) , 1283-1288. https://doi.org/10.1039/D2QO01947G
    4. Martin Linden, Silja Hofmann, Antonia Herman, Nicole Ehler, Robin M. Bär, Siegfried R. Waldvogel. Elektrochemische Synthese von Pyrazolinen und Pyrazolen via [3+2] dipolarer Cycloaddition. Angewandte Chemie 2023, 135 (9) https://doi.org/10.1002/ange.202214820
    5. Martin Linden, Silja Hofmann, Antonia Herman, Nicole Ehler, Robin M. Bär, Siegfried R. Waldvogel. Electrochemical Synthesis of Pyrazolines and Pyrazoles via [3+2] Dipolar Cycloaddition. Angewandte Chemie International Edition 2023, 62 (9) https://doi.org/10.1002/anie.202214820
    6. Kevin Lam. Electrosynthesis: A Practical Way to Access Highly Reactive Intermediates. Synlett 2022, 33 (20) , 1953-1960. https://doi.org/10.1055/a-1890-9162
    7. Saideh Rajai‐Daryasarei, Frank Rominger, Hamid Reza Bijanzadeh, Saeed Balalaie. Divergent Reaction of Allenoates: Synthesis of Polysubstituted Pyrazoles and N ‐Alkylated Hydrazones. Advanced Synthesis & Catalysis 2022, 364 (21) , 3657-3663. https://doi.org/10.1002/adsc.202200620

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