{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T19:01:55Z","timestamp":1788289315122,"version":"build-2803163510"},"reference-count":84,"publisher":"American Chemical Society (ACS)","issue":"31","license":[{"start":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T00:00:00Z","timestamp":1785369600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt Foundation","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100005156","id-type":"DOI","asserted-by":"crossref"}]},{"name":"German Research Council (DFG)","award":["TRR 325-444632635"],"award-info":[{"award-number":["TRR 325-444632635"]}]},{"DOI":"10.13039\/501100019692","name":"Leibniz Supercomputing Centre","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100019692","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Friedel\u2013Crafts alkylation is a cornerstone transformation for arene functionalization; however, strongly electron-deficient nitroarenes fail to undergo alkylation under conventional conditions. This long-standing limitation is notable given the prevalence of nitroarenes in pharmaceuticals and agrochemicals and their central role as synthetic building blocks. Here we report a photocatalytic strategy that overcomes this challenge, enabling direct C\u2013H alkylation of nitroarenes using readily available carboxylic acids as alkyl radical precursors. Under mild conditions, alkyl radicals generated through a decarboxylative process add preferentially to the aromatic \u03c0-system while preserving the nitro functionality, suppressing competing oxygen-atom transfer and reduction pathways. This transformation is compatible with a wide range of nitroarenes and carboxylic acids and tolerates diverse functional groups. Mechanistic studies support a pathway involving decarboxylative radical addition, followed by oxidation and rearomatization mediated by an organophotocatalyst. The photocatalytic strategy is also applicable to alkyltrifluoroborates as alternative alkyl radical precursors. This method enables late-stage functionalization of complex nitroarenes and bioactive molecules, providing a modular platform for sequential C\u2013H diversification and expanding the synthetic utility of nitroarenes.<\/jats:p>","DOI":"10.1021\/jacs.6c10599","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:02:10Z","timestamp":1785852130000},"page":"33683-33697","source":"Crossref","is-referenced-by-count":1,"title":["Reactivity\nof Nitroarenes toward Alkyl Radicals Enables\nDirect C\u2013H Alkylation"],"prefix":"10.1021","volume":"148","author":[{"given":"Kousik","family":"Das","sequence":"first","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sayonika","family":"Chakraborty","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6921-757X","authenticated-orcid":true,"given":"Eno","family":"Paenurk","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6131-4850","authenticated-orcid":true,"given":"Burkhard","family":"Ko\u0308nig","sequence":"additional","affiliation":[{"name":"Universita\u0308t Regensburg , , ,","place":["Regensburg, Germany, 93053"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,30]]},"reference":[{"key":"2026081210092488800_cit1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.6.6","article-title":"A review of\nnew developments in the Friedel-Crafts alkylation - From green chemistry\nto asymmetric catalysis","volume":"6","author":"Rueping","year":"2010","journal-title":"Beilstein J. Org.\nChem."},{"key":"2026081210092488800_cit2","doi-asserted-by":"publisher","first-page":"386","DOI":"10.1038\/s41557-025-02001-9","article-title":"Dearomative syn-1,4-hydroalkylation and C(sp2)-H alkylation of arenes\ncontrolled by chemoselective electrolysis","volume":"18","author":"Wan","year":"2026","journal-title":"Nat.\nChem."},{"issue":"2","key":"2026081210092488800_cit3","doi-asserted-by":"publisher","first-page":"457","DOI":"10.1021\/jo0159901","article-title":"A Three-Component\nCoupling Process Based on Vicarious Nucleophilic Substitution (VNSAR)-Alkylation\nReactions: An Approach to Indoprofen and Derivatives","volume":"67","author":"Lawrence","year":"2002","journal-title":"J. Org. Chem."},{"issue":"2","key":"2026081210092488800_cit4","doi-asserted-by":"publisher","first-page":"516","DOI":"10.1021\/acs.orglett.1c03920","article-title":"Alkylation\nof Nitropyridines via Vicarious Nucleophilic\nSubstitution","volume":"24","author":"Antoniak","year":"2022","journal-title":"Org. Lett."},{"issue":"9","key":"2026081210092488800_cit5","doi-asserted-by":"publisher","first-page":"2638","DOI":"10.1039\/D4QO00059E","article-title":"Recent\nprogress in the synthesis of N-substituted arylamines by reductive\ncross-coupling of nitroarenes","volume":"11","author":"Qin","year":"2024","journal-title":"Org. Chem. Front."},{"issue":"11","key":"2026081210092488800_cit6","doi-asserted-by":"publisher","first-page":"2254","DOI":"10.1039\/D3OB00064H","article-title":"Nitroarenes and nitroalkenes\nas potential amino sources for the synthesis of N-heterocycles","volume":"21","author":"Zou","year":"2023","journal-title":"Org. Biomol. Chem."},{"issue":"17","key":"2026081210092488800_cit7","doi-asserted-by":"publisher","first-page":"9856","DOI":"10.1021\/acscatal.0c02990","article-title":"Transition-Metal-Catalyzed\nDenitrative\nCoupling of Nitroarenes","volume":"10","author":"Muto","year":"2020","journal-title":"ACS Catal."},{"issue":"8","key":"2026081210092488800_cit8","doi-asserted-by":"publisher","first-page":"3289","DOI":"10.1007\/s11164-021-04469-9","article-title":"Chemoselective reduction of nitroarenes,\nN-acetylation of arylamines, and one-pot reductive acetylation of\nnitroarenes using carbon-supported palladium catalytic system in water","volume":"47","author":"Zeynizadeh","year":"2021","journal-title":"Res. Chem. Intermed."},{"issue":"5","key":"2026081210092488800_cit9","doi-asserted-by":"publisher","first-page":"771","DOI":"10.1038\/s41557-023-01429-1","article-title":"Synthesis\nof polysubstituted azepanes by dearomative\nring expansion of nitroarenes","volume":"16","author":"Mykura","year":"2024","journal-title":"Nat. Chem."},{"issue":"50","key":"2026081210092488800_cit10","doi-asserted-by":"publisher","first-page":"27810","DOI":"10.1021\/jacs.3c10863","article-title":"A Photochemical Strategy\nfor the Conversion of Nitroarenes into Rigidified Pyrrolidine Analogues","volume":"145","author":"Matador","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"13","key":"2026081210092488800_cit11","doi-asserted-by":"publisher","first-page":"6946","DOI":"10.1021\/acs.joc.7b00550","article-title":"Palladium Catalyzed Arylation and\nBenzylation of Nitroarenes Using Aryl Sulfonates and Benzyl Acetates","volume":"82","author":"Yi","year":"2017","journal-title":"J. Org. 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Properties and reactions of\nfree alkyl radicals\nin solution. Part XIII. Reactions with aromatic nitro-compounds","author":"Jackson","year":"1960","journal-title":"J. Chem. Soc. (Resumed)"},{"issue":"15","key":"2026081210092488800_cit33","doi-asserted-by":"publisher","first-page":"8313","DOI":"10.1002\/anie.202015740","article-title":"Fe-Catalyzed Anaerobic\nMukaiyama-Type Hydration of Alkenes using Nitroarenes","volume":"60","author":"Bhunia","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"issue":"42","key":"2026081210092488800_cit34","doi-asserted-by":"publisher","first-page":"14674","DOI":"10.1021\/ja5080739","article-title":"Enantioselective N-Heterocyclic\nCarbene-Catalyzed \u03b2-Hydroxylation\nof Enals Using Nitroarenes: An Atom Transfer Reaction That Proceeds\nvia Single Electron Transfer","volume":"136","author":"White","year":"2014","journal-title":"J. Am. Chem. Soc."},{"issue":"7","key":"2026081210092488800_cit35","doi-asserted-by":"publisher","first-page":"2416","DOI":"10.1021\/ja511371a","article-title":"N-Heterocyclic\nCarbene-Catalyzed Radical Reactions for Highly Enantioselective \u03b2-Hydroxylation\nof Enals","volume":"137","author":"Zhang","year":"2015","journal-title":"J. Am. Chem. Soc."},{"issue":"12","key":"2026081210092488800_cit36","doi-asserted-by":"publisher","first-page":"3401","DOI":"10.1016\/j.chempr.2023.09.008","article-title":"Nitroarenes: The rediscovery of their\nphotochemistry opens new avenues in organic synthesis","volume":"9","author":"Gkizis","year":"2023","journal-title":"Chem."},{"issue":"4","key":"2026081210092488800_cit37","doi-asserted-by":"publisher","DOI":"10.1002\/cptc.202300236","article-title":"The application\nof nitroarenes in\ncatalyst-free photo-driven reactions","volume":"8","author":"Teng","year":"2024","journal-title":"ChemPhotoChem."},{"issue":"32","key":"2026081210092488800_cit38","doi-asserted-by":"publisher","first-page":"9361","DOI":"10.1039\/D2SC03047K","article-title":"Photomediated reductive\ncoupling of nitroarenes with aldehydes for amide synthesis","volume":"13","author":"Li","year":"2022","journal-title":"Chem. 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Chem., Int.\nEd."},{"issue":"1","key":"2026081210092488800_cit42","doi-asserted-by":"publisher","first-page":"2432","DOI":"10.1038\/s41467-022-30176-z","article-title":"Decarboxylative tandem C-N coupling with nitroarenes\nvia SH2 mechanism","volume":"13","author":"Wang","year":"2022","journal-title":"Nat. Commun."},{"issue":"14","key":"2026081210092488800_cit43","doi-asserted-by":"publisher","first-page":"2377","DOI":"10.1002\/adsc.202300431","article-title":"Dual Nickel\/Photoredox-Catalyzed\nSynthesis of N-formyl N,N\u2019-Diaryl Ethylenediamines via Multiple\nC-N\/C-C Coupling of Nitroarenes with Trimethylamine","volume":"365","author":"Zheng","year":"2023","journal-title":"Adv. Synth. Catal."},{"issue":"1","key":"2026081210092488800_cit44","doi-asserted-by":"publisher","first-page":"9926","DOI":"10.1038\/s41467-024-53828-8","article-title":"Metallaphotocatalytic\ntriple couplings for modular\nsynthesis of elaborate N-trifluoroalkyl anilines","volume":"15","author":"Zhou","year":"2024","journal-title":"Nat. Commun."},{"key":"2026081210092488800_cit45","doi-asserted-by":"publisher","first-page":"663","DOI":"10.1021\/acs.orglett.5c04733","article-title":"Engaging Photoexcited\northo-Substituted Nitroarenes and Aryl\/Alkyl Boronic Acids in Reductive\nC-N Coupling","volume":"28","author":"Pradhan","year":"2026","journal-title":"Org. Lett."},{"issue":"14","key":"2026081210092488800_cit46","doi-asserted-by":"publisher","first-page":"9499","DOI":"10.1021\/jacs.3c14713","article-title":"Aziridination via Nitrogen-Atom Transfer to Olefins\nfrom Photoexcited Azoxy-Triazenes","volume":"146","author":"Mitchell","year":"2024","journal-title":"J. Am. Chem.\nSoc."},{"issue":"35","key":"2026081210092488800_cit47","doi-asserted-by":"publisher","first-page":"6517","DOI":"10.1021\/acs.orglett.3c02292","article-title":"Photoinduced Nitroarenes\nas Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives","volume":"25","author":"Mitchell","year":"2023","journal-title":"Org. Lett."},{"issue":"5","key":"2026081210092488800_cit48","doi-asserted-by":"publisher","first-page":"2794","DOI":"10.1021\/jacs.2c13502","article-title":"Anaerobic\nHydroxylation of C(sp3)-H Bonds Enabled by the Synergistic Nature\nof Photoexcited Nitroarenes","volume":"145","author":"Paolillo","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"24","key":"2026081210092488800_cit49","doi-asserted-by":"publisher","first-page":"4592","DOI":"10.1021\/acs.orglett.3c01694","article-title":"Nickel\/Photoredox-Catalyzed\nDirect Amidation of Aldehydes with Nitroarenes via Fully Catalytic\nProcess","volume":"25","author":"Sang","year":"2023","journal-title":"Org. Lett."},{"issue":"5","key":"2026081210092488800_cit50","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202418411","article-title":"Photooxidation\nof Polyolefins to Produce Materials with In-Chain Ketones and Improved\nMaterials Properties","volume":"64","author":"Liu","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"issue":"37","key":"2026081210092488800_cit51","doi-asserted-by":"publisher","first-page":"11074","DOI":"10.1039\/D2SC03590A","article-title":"A switchable redox\nannulation of 2-nitroarylethanols affording N-heterocycles: photoexcited\nnitro as a multifunctional handle","volume":"13","author":"Wang","year":"2022","journal-title":"Chem. Sci."},{"issue":"7930","key":"2026081210092488800_cit52","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1038\/s41586-022-05211-0","article-title":"Photoexcited nitroarenes\nfor the oxidative cleavage of alkenes","volume":"610","author":"Ruffoni","year":"2022","journal-title":"Nature"},{"issue":"6739","key":"2026081210092488800_cit53","doi-asserted-by":"publisher","first-page":"1167","DOI":"10.1126\/science.ads3955","article-title":"Excited-state configuration of nitroarenes\nenables oxidative cleavage of aromatics over alkenes","volume":"387","author":"Olivier","year":"2025","journal-title":"Science"},{"issue":"34","key":"2026081210092488800_cit54","doi-asserted-by":"publisher","first-page":"15437","DOI":"10.1021\/jacs.2c05648","article-title":"Photoinduced Oxygen Transfer Using\nNitroarenes for the Anaerobic Cleavage of Alkenes","volume":"144","author":"Wise","year":"2022","journal-title":"J. Am. Chem. Soc."},{"issue":"50","key":"2026081210092488800_cit55","doi-asserted-by":"publisher","first-page":"27810","DOI":"10.1021\/jacs.3c10863","article-title":"A Photochemical Strategy\nfor the Conversion of Nitroarenes into Rigidified Pyrrolidine Analogues","volume":"145","author":"Matador","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"6","key":"2026081210092488800_cit56","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202517867","article-title":"A General\nStrategy to Access Pharmaceutically\nRelevant Pyridines from Nitroarenes","volume":"65","author":"Saha","year":"2026","journal-title":"Angew.\nChem., Int. Ed."},{"issue":"5","key":"2026081210092488800_cit57","doi-asserted-by":"publisher","first-page":"757","DOI":"10.1021\/ja01245a006","article-title":"The Polymerization of Styrene in the Presence of Nitrobenzene,\n2,4-Dinitrochlorobenzene and Nitromethane","volume":"65","author":"Price","year":"1943","journal-title":"J.\nAm. Chem. Soc."},{"issue":"3","key":"2026081210092488800_cit58","doi-asserted-by":"publisher","first-page":"408","DOI":"10.1021\/jo01097a022","article-title":"Reactions of Nitro Compounds with 1-Cyano-1-methylethyl\nRadicals Produced by the Decomposition of \u03b1,\u03b1\u2019-Azobisisobutyronitrile","volume":"23","author":"INAMOTO","year":"1958","journal-title":"J. Org. 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