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Traditional approaches that install arenes early followed by postfunctionalization sometimes struggle to achieve diverse substitution patterns, high chemoselectivity, or satisfactory processability. As an alternative, constructing arenes via late-stage aromatization of prearomatic intermediates could offer greater flexibility, improved processability, and orthogonal reactivity, which, however, has been underdeveloped. Particularly, there remain substantial challenges of using saturated cyclohexanes as benzene precursors. Here, we report a distinct catalytic strategy that uses carboxylic acids as traceless, multifunctional anchors to achieve chemoselective, redox-neutral aromatization of cyclohexanes via transfer dehydrogenation. This approach provides a rare means to selectively aromatize carboxylated cyclohexanes even in the presence of more reactive cyclohexenes and cyclohexanones. The Ir-catalyzed protocol delivers excellent yields, remarkable chemoselectivity, and broad functional-group compatibility. Combined experimental and computational studies support an unusual mechanism involving sequential dehydrogenation, anti-decarboxylation, \u03b2-hydrogen elimination, and further dehydrogenation. The utility of the method is demonstrated in site-selective, modular syntheses of diverse multisubstituted arenes through late-stage aromatization.<\/jats:p>","DOI":"10.1021\/jacs.6c14241","type":"journal-article","created":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T22:01:50Z","timestamp":1791237710000},"page":"44757-44766","source":"Crossref","is-referenced-by-count":0,"title":["Catalytic Redox-Neutral\nDecarboxylative Aromatization\nvia Transfer Dehydrogenation"],"prefix":"10.1021","volume":"148","author":[{"given":"Yin","family":"Xu","sequence":"first","affiliation":[{"name":"University of Chicago , , , ,","place":["Chicago, Illinois, United States, 60637"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7801-5232","authenticated-orcid":true,"given":"Pei-Pei","family":"Xie","sequence":"additional","affiliation":[{"name":"University of Pittsburgh , , , ,","place":["Pittsburgh, Pennsylvania, United States, 15260"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kezhi","family":"Chen","sequence":"additional","affiliation":[{"name":"University of Chicago , , , ,","place":["Chicago, Illinois, United States, 60637"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8188-632X","authenticated-orcid":true,"given":"Peng","family":"Liu","sequence":"additional","affiliation":[{"name":"University of Pittsburgh , , , ,","place":["Pittsburgh, Pennsylvania, United States, 15260"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1331-6015","authenticated-orcid":true,"given":"Guangbin","family":"Dong","sequence":"additional","affiliation":[{"name":"University of Chicago , , , ,","place":["Chicago, Illinois, United States, 60637"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,5]]},"reference":[{"key":"2026102111085902900_cit1","doi-asserted-by":"publisher","first-page":"13389","DOI":"10.1021\/acs.jmedchem.0c00915","article-title":"Analysis of Benzenoid\nSubstitution Patterns in Small Molecule Active Pharmaceutical Ingredients","volume":"63","author":"Nilova","year":"2020","journal-title":"J. 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Chem.\nSoc."},{"key":"2026102111085902900_cit2c","doi-asserted-by":"publisher","first-page":"6439","DOI":"10.1021\/acsomega.1c05830","article-title":"Site-Selective C\u2013H Functionalization\nof Arenes Enabled by Noncovalent Interactions","volume":"7","author":"Ferna\u0301ndez-Figueiras","year":"2022","journal-title":"ACS Omega"},{"key":"2026102111085902900_cit2d","doi-asserted-by":"publisher","first-page":"10126","DOI":"10.1021\/acs.chemrev.1c00513","article-title":"Site-Selective Cross-Coupling of Polyhalogenated Arenes\nand Heteroarenes with Identical Halogen Groups","volume":"122","author":"Palani","year":"2022","journal-title":"Chem. Rev."},{"key":"2026102111085902900_cit3a","doi-asserted-by":"publisher","first-page":"10820","DOI":"10.1039\/C8CC05371E","article-title":"Development\nof a Novel Durable Aromatic Anion Exchange\nMembrane Using a Thermally Convertible Precursor","volume":"54","author":"Graha","year":"2018","journal-title":"Chem. 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Chem."},{"key":"2026102111085902900_cit12a","doi-asserted-by":"publisher","first-page":"19178","DOI":"10.1021\/jacs.5c04631","article-title":"Direct Access\nto Benzofurans and Indoles from Ethylene with 2-Methylphenols\/Anilines\nthrough Iridium-Catalyzed Dehydrogenative Annulation","volume":"147","author":"Yagi","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111085902900_cit12b","doi-asserted-by":"publisher","first-page":"155823","DOI":"10.1016\/j.tetlet.2025.155823","article-title":"Ir-Catalyzed Distal\nBranch- and Enantioselective Hydroarylation of Internal Alkenes Using\nAcetanilides via Chain-Walking and C\u2013H Activation","volume":"173","author":"Kadota","year":"2025","journal-title":"Tetrahedron Lett."},{"key":"2026102111085902900_cit12c","doi-asserted-by":"publisher","first-page":"7721","DOI":"10.1021\/jacs.4c17355","article-title":"Borrowing Hydrogen\/Chiral\nEnamine Relay Catalysis Enables Diastereo- and Enantioselective \u03b2-C\u2013H\nFunctionalization of Alcohols","volume":"147","author":"Liaw","year":"2025","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026102111085902900_cit13","doi-asserted-by":"publisher","first-page":"12357","DOI":"10.1021\/acs.chemrev.7b00247","article-title":"Dehydrogenation of Alkanes and Aliphatic\nGroups by Pincer-Ligated Metal Complexes","volume":"117","author":"Kumar","year":"2017","journal-title":"Chem.\nRev."},{"key":"2026102111085902900_cit14a","doi-asserted-by":"publisher","first-page":"9815","DOI":"10.1039\/c0dt00491j","article-title":"A DFT Study\non the Pd-Mediated Decarboxylation Process of Aryl Carboxylic Acids","volume":"39","author":"Xue","year":"2010","journal-title":"Dalton Trans."},{"key":"2026102111085902900_cit14b","doi-asserted-by":"publisher","first-page":"4744","DOI":"10.1021\/jo400222c","article-title":"Mild Aromatic Palladium-Catalyzed\nProtodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation\nand the Protodepalladation Steps","volume":"78","author":"Dickstein","year":"2013","journal-title":"J. Org. Chem."},{"key":"2026102111085902900_cit14c","doi-asserted-by":"publisher","first-page":"7224","DOI":"10.1021\/jacs.7b00714","article-title":"Mechanisms and Origins\nof Chemo- and Regioselectivities of Ru(II)-Catalyzed Decarboxylative\nC\u2013H Alkenylation of Aryl Carboxylic Acids with Alkynes: A Computational\nStudy","volume":"139","author":"Yu","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111085902900_cit15a","doi-asserted-by":"publisher","first-page":"14391","DOI":"10.1021\/ja107103b","article-title":"Palladium-Catalyzed Decarboxylative\nCouplings of 2-(2-Azaaryl)acetates with Aryl Halides and Triflates","volume":"132","author":"Shang","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111085902900_cit15b","doi-asserted-by":"publisher","first-page":"6936","DOI":"10.1021\/jacs.3c14409","article-title":"Enantioselective Cross-[4 + 2]-Cycloaddition\/Decarboxylation of 2-Pyrones\nby Cooperative Catalysis of the Pd(0)\/NHC Complex and Chiral Phosphoric\nAcid","volume":"146","author":"Xu","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111085902900_cit16a","doi-asserted-by":"publisher","first-page":"476","DOI":"10.1002\/cplu.202000005","article-title":"Regioselective C\u2013H\nFunctionalization\nof Naphthalenes: Reactivity and Mechanistic Insights","volume":"85","author":"Pre\u0301vost","year":"2020","journal-title":"ChemPlusChem"},{"key":"2026102111085902900_cit16b","doi-asserted-by":"publisher","first-page":"2600","DOI":"10.1055\/s-0040-1707855","article-title":"C\u2013H Functionalization Strategies\nin the Naphthalene Series: Site Selections and Functional Diversity","volume":"52","author":"Large","year":"2020","journal-title":"Synthesis"},{"key":"2026102111085902900_cit37c","doi-asserted-by":"crossref","DOI":"10.1002\/9783527834242.chf0227","article-title":"Directing Group-Assisted\nC\u2013H bond Functionalization on the Naphthalene","volume-title":"Handbook of CH-Functionalization","author":"Ghosh","year":"2022"},{"key":"2026102111085902900_cit16d","doi-asserted-by":"publisher","first-page":"155370","DOI":"10.1016\/j.tetlet.2024.155370","article-title":"Recent Advances in Site-Selective C\u2013H Functionalization\nof Naphthalenes: An Update 2020\u20132024","volume":"154","author":"Li","year":"2025","journal-title":"Tetrahedron Lett."},{"key":"2026102111085902900_cit17","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202500093","article-title":"Carboxylic\nAcids as Enabling Directing Groups in C\u2013H Activation and Functionalization:\nA Decade Review","volume":"367","author":"Gupta","year":"2025","journal-title":"Adv. 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Soc."},{"key":"2026102111085902900_cit20a","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1038\/nature12963","article-title":"Conformation-Induced\nRemote Meta-C\u2013H Activation of Amines","volume":"507","author":"Tang","year":"2014","journal-title":"Nature"},{"key":"2026102111085902900_cit20b","doi-asserted-by":"publisher","first-page":"5887","DOI":"10.1021\/jacs.5b02809","article-title":"Simple Amine-Directed\nMeta-Selective C\u2013H Arylation via Pd\/Norbornene Catalysis","volume":"137","author":"Dong","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111085902900_cit20c","doi-asserted-by":"publisher","first-page":"6874","DOI":"10.1002\/anie.201702686","article-title":"Ligand-Enabled\nAuxiliary-Free Meta-C\u2013H Arylation of Phenylacetic Acids","volume":"56","author":"Li","year":"2017","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026102111085902900_cit21","doi-asserted-by":"publisher","first-page":"11955","DOI":"10.1021\/jacs.2c04195","article-title":"Pd(II)-Catalyzed Synthesis of Bicyclo[3.2.1]\nLactones via Tandem Intramolecular \u03b2-C(sp3)\u2013H\nOlefination and Lactonization of Free Carboxylic Acids","volume":"144","author":"Tomanik","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111085902900_cit22","doi-asserted-by":"publisher","first-page":"3710","DOI":"10.1002\/ejoc.201100213","article-title":"Efficient Intramolecular Hydroarylation\nCatalysed by BiIII Triflate","volume":"2011","author":"Cacciuttolo","year":"2011","journal-title":"Eur.\nJ. Org. Chem."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c14241","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/41\/44757\/68750534\/jacs.6c14241.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/41\/44757\/68750534\/jacs.6c14241.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,21]],"date-time":"2026-10-21T15:15:52Z","timestamp":1792595752000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/41\/44757\/5444839\/Catalytic-Redox-Neutral-Decarboxylative"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,5]]},"references-count":46,"journal-issue":{"issue":"41","published-online":{"date-parts":[[2026,10,5]]},"published-print":{"date-parts":[[2026,10,21]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c14241","relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv.15005200\/v1","asserted-by":"object"}]},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,5]]}}}