Abstract:
An efficient electrochemical synthesis of sulfonamides (yields 56–98%) from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines was performed in an undivided cell with graphite anode and iron cathode in MeCN–H2O medium using halides as redox mediators and supporting electrolytes.
Citation:
A. O. Terent'ev, O. M. Mulina, D. A. Pirgach, M. A. Syroeshkin, A. P. Glinuskin, G. I. Nikishin, “Electrochemical synthesis of sulfonamides from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines”, Mendeleev Commun., 26:6 (2016), 538–539
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https://www.mathnet.ru/eng/mendc2273
https://www.mathnet.ru/eng/mendc/v26/i6/p538
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Wei Chen, Haojian Xu, Run Wu, Yang Chen, Pingbing Yu, Yanxi Jin, “Catalyst-free electrochemical sulfonylation of amines with sulfonyl hydrazide in aqueous medium”, Org. Biomol. Chem., 21:27 (2023), 5547
Juan Du, Ya-long Du, Qing-wen Gui, “Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions”, Synthesis, 55:18 (2023), 2799
Bao-Chen Qian, Chao-Zhe Zhu, Guang-Bin Shen, “The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies”, ACS Omega, 7:44 (2022), 39531
Kévin Saint‐Jacques, Encyclopedia of Reagents for Organic Synthesis, 2022, 1
Christina Kannigadu, Janine Aucamp, David D. N'Da, “Exploring novel nitrofuranyl sulfonohydrazides as anti‐Leishmania and anti‐cancer agents: Synthesis, in vitro efficacy and hit identification”, Chem Biol Drug Des, 100:2 (2022), 267
Nasser Amri, Thomas Wirth, “Recent Advances in the Electrochemical Synthesis of Organosulfur Compounds”, The Chemical Record, 21:9 (2021), 2526
龙 邓, “Research Progress in Electrochemical Oxidation of Sulfonyl Hydrazide”, JOCR, 09:04 (2021), 83
Mahdi Jamshidi, Ameneh Amani, Sadegh Khazalpour, Sara Torabi, Davood Nematollahi, “Progress and perspectives of electrochemical insights for C–H and N–H sulfonylation”, New J. Chem., 45:39 (2021), 18246
Haibo Mei, Romana Pajkert, Li Wang, Ziyi Li, Gerd-Volker Röschenthaler, Jianlin Han, “Chemistry of electrochemical oxidative reactions of sulfinate salts”, Green Chem., 22:10 (2020), 3028
Olga M. Mulina, Nataliya V. Zhironkina, Stanislav A. Paveliev, Dmitry V. Demchuk, Alexander O. Terent'ev, “Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides”, Org. Lett., 22:5 (2020), 1818
Man Li, Junting Hong, Wei Xiao, Yang Yang, Di Qiu, Fanyang Mo, “Electrocatalytic Oxidative Transformation of Organic Acids for Carbon–Heteroatom and Sulfur–Heteroatom Bond Formation”, ChemSusChem, 13:7 (2020), 1661
Jessy Aziz, Abdallah Hamze, “An update on the use of sulfinate derivatives as versatile coupling partners in organic chemistry”, Org. Biomol. Chem., 18:45 (2020), 9136
Stanislav A. Paveliev, Artem I. Churakov, Liliya S. Alimkhanova, Oleg O. Segida, Gennady I. Nikishin, Alexander O. Terent'ev, “Electrochemical Synthesis of O‐Phthalimide Oximes from α‐Azido Styrenes via Radical Sequence: Generation, Addition and Recombination of Imide‐N‐Oxyl and Iminyl Radicals with C-O/N-O Bonds Formation”, Adv Synth Catal, 362:18 (2020), 3864
Alexander O. Terent'ev, Olga M. Mulina, Vadim D. Parshin, Vladimir A. Kokorekin, Gennady I. Nikishin, “Electrochemically induced oxidative S–O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles”, Org. Biomol. Chem., 17:14 (2019), 3482
Hongmei Jiang, Xiaoyue Tang, Zhihui Xu, Huixian Wang, Kang Han, Xiaolan Yang, Yuanyuan Zhou, Yong-Lai Feng, Xian-Yong Yu, Qingwen Gui, “TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with tert-amines”, Org. Biomol. Chem., 17:10 (2019), 2715
A. O. Terent'ev, O. M. Mulina, A. I. Ilovaisky, V. A. Kokorekin, G. I. Nikishin, “Ammonium iodide-mediated electrosynthesis of unsymmetrical thiosulfonates from arenesulfonohydrazides and thiols”, Mendeleev Commun., 29:1 (2019), 80–82
Bo Yang, Chang Lian, Guanglu Yue, Danyang Liu, Liyan Wei, Yi Ding, Xiancai Zheng, Kui Lu, Di Qiu, Xia Zhao, “Synthesis of N-arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates”, Org. Biomol. Chem., 16:43 (2018), 8150
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