{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T03:56:55Z","timestamp":1790913415700,"version":"4.1.0"},"reference-count":116,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2021,10,22]],"date-time":"2021-10-22T00:00:00Z","timestamp":1634860800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["Wa1276\/17-2"],"award-info":[{"award-number":["Wa1276\/17-2"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemSusChem"],"published-print":{"date-parts":[[2021,11,19]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu<jats:sub>4<\/jats:sub>NO<jats:sub>2<\/jats:sub>, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy\u2010to\u2010handle nitro source. Stoichiometric amounts of 1,1,1\u20103,3,3\u2010hexafluoroisopropan\u20102\u2010ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO<jats:sub>2<\/jats:sub>, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88\u2009%. Scalability is demonstrated by a 13\u2010fold scale\u2010up.<\/jats:p>","DOI":"10.1002\/cssc.202102053","type":"journal-article","created":{"date-parts":[[2021,9,28]],"date-time":"2021-09-28T17:10:49Z","timestamp":1632849049000},"page":"4936-4940","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":41,"title":["Electrochemical Nitration with Nitrite"],"prefix":"10.1002","volume":"14","author":[{"given":"Stephan P.","family":"Blum","sequence":"first","affiliation":[{"name":"Department of Chemistry Johannes Gutenberg University Mainz  Duesbergweg 10\u201314 55128 Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christean","family":"Nickel","sequence":"additional","affiliation":[{"name":"Department of Chemistry Johannes Gutenberg University Mainz  Duesbergweg 10\u201314 55128 Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lukas","family":"Sch\u00e4ffer","sequence":"additional","affiliation":[{"name":"Department of Chemistry Johannes Gutenberg University Mainz  Duesbergweg 10\u201314 55128 Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tarik","family":"Karakaya","sequence":"additional","affiliation":[{"name":"Department of Chemistry Johannes Gutenberg University Mainz  Duesbergweg 10\u201314 55128 Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7949-9638","authenticated-orcid":false,"given":"Siegfried R.","family":"Waldvogel","sequence":"additional","affiliation":[{"name":"Department of Chemistry Johannes Gutenberg University Mainz  Duesbergweg 10\u201314 55128 Mainz Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,10,22]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1128\/MMBR.00006-10"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202004695"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471224480"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob27354g"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02750A"},{"key":"e_1_2_2_7_2","volume-title":"Nitro Compounds, Aromatic in Ullmann's Encyclopedia of Industrial Chemistry","author":"Booth G.","year":"2000"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4gc00166d"},{"key":"e_1_2_2_9_1","unstructured":"\u00a0"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.8b00147"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00436-006-0431-5"},{"key":"e_1_2_2_12_2","unstructured":"Data obtained from DrugBank Online (accessed on August 26th 2021)."},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","first-page":"67","volume":"14","author":"Wang A. L.","year":"2017","journal-title":"J. Geriatr. Cardiol."},{"key":"e_1_2_2_15_2","doi-asserted-by":"crossref","unstructured":"A.\u2005I. Meyers T. Oppenlaender J. Chem. Soc Chem. Commun.1986 920\u2013921.","DOI":"10.1039\/c39860000920"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx7001349"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC01848A"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1557\/mre.2020.42"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202014544"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711060"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711060"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00233"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202016164"},{"key":"e_1_2_2_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202016164"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202001180"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC03018C"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00397"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0GC01247E"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00578"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00656"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712732"},{"key":"e_1_2_2_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201712732"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/celc.201900435"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-14322-z"},{"key":"e_1_2_2_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC03784G"},{"key":"e_1_2_2_35_1","unstructured":"\u00a0"},{"key":"e_1_2_2_36_2","first-page":"1","volume-title":"Nitration, ACS Symposium Series, Vol. 623","author":"Albright L. F.","year":"1996"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jlp.2009.08.017"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11814-012-0173-2"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.trac.2012.07.013"},{"key":"e_1_2_2_41_1","unstructured":"\u00a0"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CC37481A"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ed100957v"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol901731w"},{"key":"e_1_2_2_45_2","first-page":"753","volume":"34","author":"Akhlaghinia B.","year":"2010","journal-title":"Turk. J. Chem."},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201900664"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.09.140"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2019.151529"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo800839f"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01028"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1080\/10426500490274655"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b01384"},{"key":"e_1_2_2_53_1","unstructured":"\u00a0"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB00337G"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja905768k"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra45118f"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300325t"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200906940"},{"key":"e_1_2_2_58_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200906940"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0493249"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.01.138"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2000-7642"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397911.2016.1244690"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc15484b"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b03289"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00671"},{"key":"e_1_2_2_66_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-11419-y"},{"key":"e_1_2_2_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b03260"},{"key":"e_1_2_2_68_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202000267"},{"key":"e_1_2_2_69_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202100363"},{"key":"e_1_2_2_70_1","unstructured":"\u00a0"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-0728(87)80009-8"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-0728(99)00232-6"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1590\/S0103-50531997000400010"},{"key":"e_1_2_2_74_1","unstructured":"\u00a0"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jelechem.2006.11.026"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.electacta.2017.10.151"},{"key":"e_1_2_2_77_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01837"},{"key":"e_1_2_2_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.197819781208"},{"key":"e_1_2_2_79_1","unstructured":"\u00a0"},{"key":"e_1_2_2_80_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00757D"},{"key":"e_1_2_2_81_2","first-page":"1","volume-title":"Radicals in Synthesis III","author":"Waldvogel S. R.","year":"2012"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/celc.201801620"},{"key":"e_1_2_2_83_1","first-page":"275","volume":"30","author":"Schulz L.","year":"2018","journal-title":"Synlett"},{"key":"e_1_2_2_84_1","unstructured":"\u00a0"},{"key":"e_1_2_2_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00233"},{"key":"e_1_2_2_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00511"},{"key":"e_1_2_2_87_2","first-page":"252","volume":"49","author":"Riehl B.","year":"2017","journal-title":"Synthesis"},{"key":"e_1_2_2_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201808555"},{"key":"e_1_2_2_88_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201808555"},{"key":"e_1_2_2_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102182"},{"key":"e_1_2_2_90_1","unstructured":"\u00a0"},{"key":"e_1_2_2_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/op0200120"},{"key":"e_1_2_2_92_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200303111"},{"key":"e_1_2_2_93_1","doi-asserted-by":"publisher","DOI":"10.1002\/celc.201901212"},{"key":"e_1_2_2_94_1","unstructured":"\u00a0"},{"key":"e_1_2_2_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00268a036"},{"key":"e_1_2_2_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja001318u"},{"key":"e_1_2_2_97_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00091a018"},{"key":"e_1_2_2_98_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2010.09.057"},{"key":"e_1_2_2_99_1","unstructured":"\u00a0"},{"key":"e_1_2_2_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo950814b"},{"key":"e_1_2_2_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.est.8b01161"},{"key":"e_1_2_2_102_1","doi-asserted-by":"crossref","unstructured":"L. Eberson M.\u2005P. Hartshorn O. Persson F. Radner Chem. Commun.1996 2105\u20132112.","DOI":"10.1039\/cc9960002105"},{"key":"e_1_2_2_103_1","unstructured":"\u00a0"},{"key":"e_1_2_2_104_2","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1021\/ba-1988-0217.ch009","volume-title":"Polynuclear Aromatic Compounds, Advances in Chemistry, Vol. 217","author":"Ross D. S.","year":"1987"},{"key":"e_1_2_2_105_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397910802136706"},{"key":"e_1_2_2_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/jccs.200800106"},{"key":"e_1_2_2_107_2","doi-asserted-by":"publisher","DOI":"10.1081\/SCC-120016310"},{"key":"e_1_2_2_108_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01545a023"},{"key":"e_1_2_2_109_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01578a074"},{"key":"e_1_2_2_110_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp8029924"},{"key":"e_1_2_2_111_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00750-X"}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.202102053","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cssc.202102053","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.202102053","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T17:52:00Z","timestamp":1760377920000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.202102053"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,10,22]]},"references-count":116,"journal-issue":{"issue":"22","published-print":{"date-parts":[[2021,11,19]]}},"alternative-id":["10.1002\/cssc.202102053"],"URL":"https:\/\/doi.org\/10.1002\/cssc.202102053","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,10,22]]},"assertion":[{"value":"2021-09-27","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-10-22","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}