{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,26]],"date-time":"2026-10-26T20:59:07Z","timestamp":1793048347578,"version":"4.5.0"},"reference-count":43,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T00:00:00Z","timestamp":1788134400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100006734","name":"Princeton University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100006734","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R35GM134897"],"award-info":[{"award-number":["R35GM134897"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Princeton Catalysis Initiative"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Alkene hydroarylation provides a direct strategy for merging aryl groups with alkene-derived C(sp3)-rich fragments, yet general methods that employ abundant aryl bromides across diverse alkene classes remain elusive. Herein, we report XAT-Heck, a radical hydroarylation platform that couples aryl bromides with alkenes under mild photoredox conditions through halogen-atom transfer (XAT)-enabled aryl radical generation. The method accommodates terminal, internal, and gem-disubstituted alkenes, as well as a broad range of heteroaryl and aryl bromides. Chemical-space mapping further supports the broad coverage of commercially available olefin and aryl bromide space. The versatility of this platform is showcased through deuterium incorporation, medium-ring formation, late-stage functionalization, and proteolysis-targeting chimera (PROTAC) library construction.<\/jats:p>","DOI":"10.1021\/jacs.6c14333","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T04:50:51Z","timestamp":1788411051000},"page":"38588-38596","source":"Crossref","is-referenced-by-count":1,"title":["A General Photoredox\nPlatform for the Hydroarylation\nof Olefins"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4719-0879","authenticated-orcid":true,"given":"Yi-Lun","family":"Li","sequence":"first","affiliation":[{"name":"Merck Center for Catalysis at Princeton University , , ,","place":["Princeton, New Jersey, United States, 08544"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5021-681X","authenticated-orcid":true,"given":"Johnny Z.","family":"Wang","sequence":"additional","affiliation":[{"name":"Merck Center for Catalysis at Princeton University , , ,","place":["Princeton, New Jersey, United States, 08544"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6447-0587","authenticated-orcid":true,"given":"David W. C.","family":"MacMillan","sequence":"additional","affiliation":[{"name":"Merck Center for Catalysis at Princeton University , , ,","place":["Princeton, New Jersey, United States, 08544"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,31]]},"reference":[{"issue":"13","key":"2026091609125774800_cit1","doi-asserted-by":"publisher","first-page":"8643","DOI":"10.1021\/acs.jmedchem.3c00275","article-title":"Escaping from\nFlatland: Multiparameter Optimization Leads to the Discovery of Novel\nTetrahydropyrido[4,3-d]Pyrimidine Derivatives as Human Immunodeficiency\nVirus-1 Non-Nucleoside Reverse Transcriptase Inhibitors with Superior\nAntiviral Activities against Non-Nucleoside Reverse Transcriptase\nInhibitor-Resistant Variants and Favorable Drug-like Profiles","volume":"66","author":"Wang","year":"2023","journal-title":"J. Med. Chem."},{"issue":"3","key":"2026091609125774800_cit2","doi-asserted-by":"publisher","first-page":"515","DOI":"10.1039\/c2md20347b","article-title":"Escape from\nFlatland 2: Complexity and Promiscuity","volume":"4","author":"Lovering","year":"2013","journal-title":"Medchemcomm"},{"issue":"14","key":"2026091609125774800_cit3","doi-asserted-by":"publisher","first-page":"7736","DOI":"10.1021\/jacs.3c01488","article-title":"Expedient\nAccess to Underexplored Chemical Space: Deoxygenative\nC(Sp3)-C(Sp3) Cross-Coupling","volume":"145","author":"Lyon","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"6334","key":"2026091609125774800_cit4","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf7230","article-title":"Transition\nMetal-Catalyzed Alkyl-Alkyl Bond Formation: Another Dimension\nin Cross-Coupling Chemistry","volume":"356","author":"Choi","year":"2017","journal-title":"Science (1979)."},{"issue":"4","key":"2026091609125774800_cit5","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1038\/s41557-018-0021-z","article-title":"Organic Synthesis Provides Opportunities\nto Transform Drug Discovery","volume":"10","author":"Blakemore","year":"2018","journal-title":"Nat. Chem."},{"issue":"6","key":"2026091609125774800_cit6","doi-asserted-by":"publisher","first-page":"1239","DOI":"10.1111\/j.1476-5381.2010.01127.x","article-title":"Principles of Early\nDrug Discovery","volume":"162","author":"Hughes","year":"2011","journal-title":"Br. J. Pharmacol."},{"issue":"5","key":"2026091609125774800_cit7","doi-asserted-by":"publisher","first-page":"585","DOI":"10.1021\/ar800183j","article-title":"Ru(II)\nCatalysts Supported by Hydridotris(Pyrazolyl)Borate for the Hydroarylation\nof Olefins: Reaction Scope, Mechanistic Studies, and Guides for the\nDevelopment of Improved Catalysts","volume":"42","author":"Foley","year":"2009","journal-title":"Acc. Chem.\nRes."},{"issue":"10","key":"2026091609125774800_cit8","doi-asserted-by":"publisher","first-page":"826","DOI":"10.1021\/ar960318p","article-title":"Catalytic C-H\/Olefin Coupling","volume":"35","author":"Kakiuchi","year":"2002","journal-title":"Acc. Chem. Res."},{"issue":"6","key":"2026091609125774800_cit9","doi-asserted-by":"publisher","first-page":"572","DOI":"10.1016\/j.trechm.2019.05.007","article-title":"Palladium-Catalyzed\nReductive Heck Coupling of Alkenes","volume":"1","author":"Oxtoby","year":"2019","journal-title":"Trends Chem."},{"issue":"28","key":"2026091609125774800_cit10","doi-asserted-by":"publisher","first-page":"8718","DOI":"10.1021\/jacs.6b05271","article-title":"Intermolecular\nHydropyridylation of Unactivated Alkenes","volume":"138","author":"Ma","year":"2016","journal-title":"J.\nAm. Chem. Soc."},{"issue":"39","key":"2026091609125774800_cit11","doi-asserted-by":"publisher","first-page":"12779","DOI":"10.1021\/jacs.6b08507","article-title":"Branch-Selective\nHydroarylation: Iodoarene-Olefin Cross-Coupling","volume":"138","author":"Green","year":"2016","journal-title":"J. Am. Chem. Soc."},{"issue":"16","key":"2026091609125774800_cit12","doi-asserted-by":"publisher","first-page":"4747","DOI":"10.1002\/slct.201804029","article-title":"Reductive\nHeck Reaction: An Emerging Alternative in Natural Product Synthesis","volume":"4","author":"Ghosh","year":"2019","journal-title":"ChemistrySelect"},{"key":"2026091609125774800_cit13","doi-asserted-by":"publisher","first-page":"249","DOI":"10.1016\/0022-328X(89)85320-3","article-title":"Palladium-Catalyzed\nPreparation of Exo-Aryl Derivatives of the Norbornane Skeleton","volume":"368","author":"Arcadi","year":"1989","journal-title":"J. Organomet. Chem."},{"key":"2026091609125774800_cit14","doi-asserted-by":"publisher","first-page":"C21","DOI":"10.1016\/S0022-328X(00)84537-4","article-title":"New Transition-Metal-Catalyzed\nC-C Coupling Reactions Initiated by C-X Bond Cleavage and Terminated\nby H-Transfer","volume":"199","author":"Catellani","year":"1980","journal-title":"J. Organomet. Chem."},{"issue":"45","key":"2026091609125774800_cit15","doi-asserted-by":"publisher","first-page":"5752","DOI":"10.1039\/C8CC02571A","article-title":"Pd-Catalyzed Reductive Heck Reaction\nof Olefins with Aryl Bromides\nfor Csp2-Csp3 Bond Formation","volume":"54","author":"Jin","year":"2018","journal-title":"Chem. Commun."},{"issue":"11","key":"2026091609125774800_cit16","doi-asserted-by":"publisher","first-page":"3231","DOI":"10.1039\/C8SC05445B","article-title":"Nickel-Catalyzed\nAnti-Markovnikov\nHydroarylation of Alkenes","volume":"10","author":"Nguyen","year":"2019","journal-title":"Chem. 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Soc."},{"key":"2026091609125774800_cit20","doi-asserted-by":"publisher","first-page":"7242","DOI":"10.1002\/anie.201703400","article-title":"A Dual Palladium\nand Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling\nof Aryl Halides and Olefins","volume":"56","author":"Friis","year":"2017","journal-title":"Angew. Chem., Int.\nEd."},{"issue":"16","key":"2026091609125774800_cit21","doi-asserted-by":"publisher","first-page":"6898","DOI":"10.1021\/acs.joc.6b01449","article-title":"Photoredox Catalysis in Organic Chemistry","volume":"81","author":"Shaw","year":"2016","journal-title":"J. Org. Chem."},{"issue":"7","key":"2026091609125774800_cit22","doi-asserted-by":"publisher","first-page":"5322","DOI":"10.1021\/cr300503r","article-title":"Visible\nLight Photoredox Catalysis\nwith Transition Metal Complexes: Applications in Organic Synthesis","volume":"113","author":"Prier","year":"2013","journal-title":"Chem. 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Soc."},{"key":"2026091609125774800_cit32","doi-asserted-by":"publisher","first-page":"1010","DOI":"10.1126\/science.aat4133","article-title":"A Radical\nApproach to the Copper Oxidative Addition Problem: Trifluoromethylation\nof Bromoarenes","volume":"360","author":"Le","year":"2018","journal-title":"Science"},{"key":"2026091609125774800_cit33","unstructured":"SMILES strings for olefins and aryl bromides\nin the Enamine catalogue\nwere retrieved from the Enamine website: https:\/\/enamine.net\/building-blocks\/functional-classes (accessed 2025-12-01)."},{"key":"2026091609125774800_cit34","doi-asserted-by":"publisher","DOI":"10.48550\/arXiv.1802.03426","article-title":"UMAP: Uniform Manifold Approximation\nand Projection for Dimension Reduction","author":"McInnes","year":"2020","journal-title":"arXiv"},{"key":"2026091609125774800_cit35","doi-asserted-by":"crossref","unstructured":"McInnes, L.; Healy, J.\n          Accelerated Hierarchical\nDensity\nBased Clustering. 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Rev. Drug Discovery"},{"issue":"5","key":"2026091609125774800_cit43","doi-asserted-by":"publisher","first-page":"273","DOI":"10.37349\/etat.2020.00018","article-title":"Current Strategies for the Design\nof PROTAC Linkers: A Critical Review","volume":"1","author":"Troup","year":"2020","journal-title":"Explor.\nTarget. Antitumor Ther."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c14333","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/36\/38588\/68021106\/jacs.6c14333.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/36\/38588\/68021106\/jacs.6c14333.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T14:09:07Z","timestamp":1789567747000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/36\/38588\/5387624\/A-General-Photoredox-Platform-for-the"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,31]]},"references-count":43,"journal-issue":{"issue":"36","published-online":{"date-parts":[[2026,8,31]]},"published-print":{"date-parts":[[2026,9,16]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c14333","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,31]]}}}