{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T06:38:42Z","timestamp":1792478322165,"version":"4.5.0"},"reference-count":47,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T00:00:00Z","timestamp":1790380800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T00:00:00Z","timestamp":1790380800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100007611","name":"Shiv Nadar University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100007611","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":[[2026,10,14]]},"abstract":"<jats:p>We report a catalyst\u2010, acid\u2010, and base\u2010free strategy for activation of an N\u2013N\u2010containing diaziridine\/diazo\u2010derived framework enabling the synthesis of unsymmetrical azobenzenes via a mechanochemical three\u2010component reaction in a horizontal bead mill (DYNO\u2010MILL). The process proceeds through in situ formation of a diaziridine intermediate from a formal 2\u2009+\u20091 annulation of diazo esters and dialkyl azodicarboxylates, followed by electrophile\u2010induced N\u2500N bond reorganization with aryl diazonium tetrafluoroborates. This solvent\u2010minimized, operationally simple protocol tolerates air and moisture and is scalable. The resulting azobenzenes serve as versatile substrates for oxidant\u2010free electrochemical conversion to substituted tetrazoles without chromatographic purification. Green metrics analysis for the tetrazole formation reveals a significant improvement in atom economy (77.33%) compared to literature methods (29.98%\u201334.96%) and an enhanced Eco\u2010Scale score (73), highlighting the sustainability of this approach.<\/jats:p>","DOI":"10.1002\/cssc.71115","type":"journal-article","created":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T10:09:17Z","timestamp":1790417357000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["DYNO\u2010MILL Mechanochemistry Enables Diaziridine\u2010Mediated Access to Unsymmetrical Azobenzenes and Electrochemical Tetrazole Synthesis"],"prefix":"10.1002","volume":"19","author":[{"given":"Haya","family":"Khan","sequence":"first","affiliation":[{"name":"Department of Chemistry School of Natural Sciences Shiv Nadar Institution of Eminence, Deemed to be University  Dadri Uttar Pradesh India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4608-5498","authenticated-orcid":false,"given":"Subhabrata","family":"Sen","sequence":"additional","affiliation":[{"name":"Department of Chemistry School of Natural Sciences Shiv Nadar Institution of Eminence, Deemed to be University  Dadri Uttar Pradesh India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,26]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00183j"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.v43:40"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15023e"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15179G"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/chin.v34:22"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300179f"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.v1:1"},{"key":"e_1_2_9_9_1","first-page":"506","article-title":"\u00dcber Die Reduction Von Nitrobenzol Mit Wasserstoff","volume":"6","author":"Haber F.","year":"1900","journal-title":"Zeitschrift f\u00fcr Elektrochemie"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010022\u201035613\u20107"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/CT8956700925"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00945A"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CY01015B"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.01.048"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/c005219c"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.v15:4"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0509861"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.v61.40"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3QO01425H"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol5027014"},{"key":"e_1_2_9_21_1","volume-title":"Compendium of Chemical Terminology","author":"IUPAC","year":"1997"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/B815174A"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/b915744c"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/9781782621980-00241"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mineng.2012.07.015"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ces.2004.07.020"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.0c00521"},{"key":"e_1_2_9_28_1","doi-asserted-by":"crossref","unstructured":"N.Biedermann P. M. C.Roth andM.Schn\u00fcrch \u201cFrom Ball\u2010Milling to Bead\u2010Milling Technology: Short Time Optimization and Scale\u2010up of a One\u2010Pot Wittig Olefination\u2010Diels\u2010Alder Reaction Sequence Using an Agitator Bead Mill \u201d2026) ChemRxiv Preprint https:\/\/doi.org\/10.26434\/chemrxiv.10001739\/v1.","DOI":"10.26434\/chemrxiv.10001739\/v1"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5GC04764A"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.v17.12"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5QO00851D"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2026.103098"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5c00144"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4GC02565B"},{"key":"e_1_2_9_35_1","first-page":"621","volume-title":"Comprehensive Heterocyclic Chemistry","author":"Butler R. N.","year":"1996"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0968\u20100896(02)00239\u20100"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10593\u2010007\u20100001\u20105"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-008096519-2.00081-3"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1070\/RC2006v075n06ABEH003601"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.v49:39"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc17894j"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC07324C"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5QO00840A"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00813a015"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00406"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.7b03505"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1186\/1860\u20105397\u20102\u20103"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022\u20101139(00)00337\u20107"}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.71115","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cssc.71115","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.71115","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T05:40:30Z","timestamp":1792474830000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.71115"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,26]]},"references-count":47,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2026,10,14]]}},"alternative-id":["10.1002\/cssc.71115"],"URL":"https:\/\/doi.org\/10.1002\/cssc.71115","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,26]]},"assertion":[{"value":"2026-05-23","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-17","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-26","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71115"}}