{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T14:08:29Z","timestamp":1789567709806,"version":"build-2803163510"},"reference-count":77,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T00:00:00Z","timestamp":1788393600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100001082","name":"Camille and Henry Dreyfus Foundation","doi-asserted-by":"publisher","award":["TC-23-048"],"award-info":[{"award-number":["TC-23-048"]}],"id":[{"id":"10.13039\/100001082","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R35GM138165"],"award-info":[{"award-number":["R35GM138165"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"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>Multicomponent cross-coupling reactions of alkenes offer a powerful strategy for constructing three-dimensional, sp3 -rich molecular architectures, a key objective in modern medicinal chemistry. However, the regioselective dicarbofunctionalization of unactivated alkenes without the use of directing groups remains a significant challenge. Herein, we report a visible-light-induced, Ni-catalyzed platform that enables the radical 1,2-dicarbofunctionalization of unactivated alkenes using diverse alkyl radical precursors and aryl, vinyl, acyl, alkynyl, and alkyl coupling partners. Mechanistic studies support a catalytic cycle in which multiple electron donor\u2013acceptor (EDA) complexes mediate radical generation, atom-transfer radical addition (ATRA), and cross-electrophile coupling (XEC) or bimolecular homolytic substitution (SH2) processes. Additionally, preferential formation of a complex between the Ni catalyst and the radical precursor suppresses undesired homocoupling of the electrophilic partner. Notably, delivery of gaseous radical precursors such as trifluoromethyl iodide (TFMI) from the robust metal\u2013organic framework (MOF) Al(OH)fum (fum\u2013 = fumarate) or Al\u2013fum offers advantages in terms of both operational safety and reaction efficiency, and the MOF further boosts the yields of reactions by decreasing the concentration of free amine (employed for radical generation) in solution. Collectively, this flexible, directing-group-free approach establishes a general platform for the rapid construction of structurally complex and pharmaceutically relevant molecules from readily available precursors.<\/jats:p>","DOI":"10.1021\/jacs.6c10952","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T19:15:36Z","timestamp":1788462936000},"page":"38941-38954","source":"Crossref","is-referenced-by-count":0,"title":["Modular\nPlatform for Directing-Group-Free Radical\nDicarbofunctionalization of Unactivated Alkenes via Dual Nickel\/Energy-Transfer\nCatalysis"],"prefix":"10.1021","volume":"148","author":[{"given":"Jiachen","family":"He","sequence":"first","affiliation":[{"name":"Cornell University , , , ,","place":["Ithaca, New York, United States, 14850"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oliver P.","family":"Lambert","sequence":"additional","affiliation":[{"name":"Cornell University , , , ,","place":["Ithaca, New York, United States, 14850"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yihuan","family":"Lai","sequence":"additional","affiliation":[{"name":"Cornell University , , , ,","place":["Ithaca, New York, United States, 14850"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2618-013X","authenticated-orcid":true,"given":"Phillip J.","family":"Milner","sequence":"additional","affiliation":[{"name":"Cornell University , , , ,","place":["Ithaca, New York, United States, 14850"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,3]]},"reference":[{"issue":"3","key":"2026091609115244500_cit1","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":"21","key":"2026091609115244500_cit2","doi-asserted-by":"publisher","first-page":"6752","DOI":"10.1021\/jm901241e","article-title":"Escape from\nFlatland: Increasing\nSaturation as an Approach to Improving Clinical Success","volume":"52","author":"Lovering","year":"2009","journal-title":"J. Med. Chem."},{"issue":"14","key":"2026091609115244500_cit3","doi-asserted-by":"publisher","first-page":"6726","DOI":"10.1039\/D5CS00181A","article-title":"Navigating\nthe Functionalization of Unactivated Alkenes via Visible\nLight Photocatalysis","volume":"54","author":"Cao","year":"2025","journal-title":"Chem. Soc. Rev."},{"issue":"20","key":"2026091609115244500_cit4","doi-asserted-by":"publisher","first-page":"9530","DOI":"10.1039\/D5CS00670H","article-title":"Intermolecular\n1,2-Difunctionalization of Alkenes","volume":"54","author":"Wang","year":"2025","journal-title":"Chem. Soc.\nRev."},{"issue":"6","key":"2026091609115244500_cit5","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.202400263","article-title":"Electrochemical\nDifunctionalization of Alkenes","volume":"25","author":"Zhang","year":"2025","journal-title":"Chem. Rec."},{"issue":"6","key":"2026091609115244500_cit6","doi-asserted-by":"publisher","first-page":"2913","DOI":"10.1039\/D5SC08771F","article-title":"Radical Docking\u2013Migration:\nA Powerful Strategy for Difunctionalization of Alkenes and Alkynes","volume":"17","author":"Cao","year":"2026","journal-title":"Chem. Sci."},{"issue":"19","key":"2026091609115244500_cit7","doi-asserted-by":"publisher","first-page":"10836","DOI":"10.1039\/D1CS00399B","article-title":"Catalytic Three-Component\nDicarbofunctionalization Reactions Involving Radical Capture by Nickel","volume":"50","author":"Zhu","year":"2021","journal-title":"Chem. Soc. Rev."},{"issue":"15","key":"2026091609115244500_cit8","doi-asserted-by":"publisher","first-page":"8542","DOI":"10.1021\/acscatal.0c02115","article-title":"Nickel-Catalyzed Dicarbofunctionalization\nof Alkenes","volume":"10","author":"Qi","year":"2020","journal-title":"ACS Catal"},{"issue":"17","key":"2026091609115244500_cit9","doi-asserted-by":"publisher","first-page":"3415","DOI":"10.1021\/acs.accounts.1c00329","article-title":"Transition Metal (Ni,\nCu, Pd)-Catalyzed Alkene Dicarbofunctionalization\nReactions","volume":"54","author":"Wickham","year":"2021","journal-title":"Acc. Chem. Res."},{"issue":"17","key":"2026091609115244500_cit10","doi-asserted-by":"publisher","first-page":"4287","DOI":"10.1039\/C9SC06006E","article-title":"Recent\nDevelopments in Nickel-Catalyzed Intermolecular Dicarbofunctionalization\nof Alkenes","volume":"11","author":"Derosa","year":"2020","journal-title":"Chem. Sci."},{"issue":"24","key":"2026091609115244500_cit11","doi-asserted-by":"publisher","first-page":"3637","DOI":"10.1002\/cjoc.70231","article-title":"Recent Progress\non Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes","volume":"43","author":"Liu","year":"2025","journal-title":"Chin. J. Chem."},{"issue":"6","key":"2026091609115244500_cit12","doi-asserted-by":"publisher","first-page":"100901","DOI":"10.1016\/j.xcrp.2022.100901","article-title":"Directing Group-Free\nApproaches for Three-Component\nCatalytic Dicarbofunctionalization of Unactivated Alkenes","volume":"3","author":"Wang","year":"2022","journal-title":"Cell Rep. Phys. Sci."},{"issue":"31","key":"2026091609115244500_cit13","doi-asserted-by":"publisher","first-page":"10657","DOI":"10.1021\/jacs.7b06567","article-title":"Nickel-Catalyzed\n\u03b2,\u03b3-Dicarbofunctionalization of Alkenyl Carbonyl Compounds\nvia Conjunctive Cross-Coupling","volume":"139","author":"Derosa","year":"2017","journal-title":"J. Am. 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Am. Chem. Soc."},{"issue":"46","key":"2026091609115244500_cit18","doi-asserted-by":"publisher","first-page":"15586","DOI":"10.1021\/jacs.8b09401","article-title":"Synergistic\nBimetallic Ni\/Ag and Ni\/Cu Catalysis for Regioselective \u03b3,\u03b4-Diarylation\nof Alkenyl Ketimines: Addressing \u03b2-H Elimination by in Situ\nGeneration of Cationic Ni(II) Catalysts","volume":"140","author":"Basnet","year":"2018","journal-title":"J.\nAm. Chem. Soc."},{"issue":"4","key":"2026091609115244500_cit19","doi-asserted-by":"publisher","first-page":"904","DOI":"10.1039\/C7SC04351A","article-title":"Ni-Catalysed Regioselective\n1,2-Diarylation of Unactivated Olefins\nby Stabilizing Heck Intermediates as Pyridylsilyl-Coordinated Transient\nMetallacycles","volume":"9","author":"Thapa","year":"2018","journal-title":"Chem. 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Lett."},{"issue":"42","key":"2026091609115244500_cit39","doi-asserted-by":"publisher","first-page":"28624","DOI":"10.1021\/jacs.4c10204","article-title":"Regiodivergent Radical-Relay Alkene\nDicarbofunctionalization","volume":"146","author":"Liu","year":"2024","journal-title":"J. Am. Chem. Soc."},{"issue":"11","key":"2026091609115244500_cit40","doi-asserted-by":"publisher","first-page":"6308","DOI":"10.1039\/D1CS00200G","article-title":"Radical Trifluoromethylation","volume":"50","author":"Xiao","year":"2021","journal-title":"Chem. Soc. Rev"},{"issue":"9","key":"2026091609115244500_cit41","doi-asserted-by":"publisher","first-page":"1163","DOI":"10.1039\/C6QO00153J","article-title":"Recent Advances\nin Photoinduced Trifluoromethylation\nand Difluoroalkylation","volume":"3","author":"Pan","year":"2016","journal-title":"Org. Chem. Front"},{"issue":"29","key":"2026091609115244500_cit42","doi-asserted-by":"publisher","first-page":"10202","DOI":"10.1021\/ja504458j","article-title":"Copper-Catalyzed\nIntermolecular Trifluoromethylarylation of Alkenes: Mutual Activation\nof Arylboronic Acid and CF3+ Reagent","volume":"136","author":"Wang","year":"2014","journal-title":"J. Am. Chem. Soc."},{"issue":"13","key":"2026091609115244500_cit43","doi-asserted-by":"publisher","first-page":"5341","DOI":"10.1021\/acs.orglett.9b01992","article-title":"Visible-Light-Mediated\nIodoperfluoroalkylation of Alkenes in Flow and Its Application to\nthe Synthesis of a Key Fulvestrant Intermediate","volume":"21","author":"Rosso","year":"2019","journal-title":"Org. Lett."},{"issue":"22","key":"2026091609115244500_cit44","doi-asserted-by":"publisher","first-page":"9106","DOI":"10.1021\/ja303514b","article-title":"Nickel-Catalyzed\nCarboxylation of Aryl and Vinyl Chlorides Employing Carbon Dioxide","volume":"134","author":"Fujihara","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026091609115244500_cit45","doi-asserted-by":"publisher","first-page":"135156","DOI":"10.1016\/j.tet.2026.135156","article-title":"Perfluoroalkylation\nReactions via Halogen-Bonded Electron\nDonor-Acceptor (EDA) Complexes of Amines and Perfluoroalkyl Halides\nunder Visible Light","volume":"193","author":"Tagami","year":"2026","journal-title":"Tetrahedron"},{"issue":"15","key":"2026091609115244500_cit46","doi-asserted-by":"publisher","first-page":"5450","DOI":"10.1039\/D1SC00943E","article-title":"Photoactive Electron\nDonor\u2013Acceptor Complex Platform for Ni-Mediated C(Sp3)\u2013C(Sp2) Bond Formation","volume":"12","author":"Kammer","year":"2021","journal-title":"Chem. Sci."},{"issue":"20","key":"2026091609115244500_cit47","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.202200918","article-title":"Nickel and Palladium\nCatalyzed C\u2013H Trifluoromethylation Using Trifluoromethyliodide:\nInvestigations into New Reactivity","volume":"14","author":"Solomon","year":"2022","journal-title":"ChemCatchem"},{"issue":"19","key":"2026091609115244500_cit48","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202203499","article-title":"Carbotrifluoromethylations of C\u2013C Multiple Bonds (Excluding\nAryl- and Alkynyltrifluoromethylations)","volume":"29","author":"Aradi","year":"2023","journal-title":"Chem.\nEur. J."},{"issue":"14","key":"2026091609115244500_cit49","doi-asserted-by":"publisher","first-page":"11622","DOI":"10.1021\/acs.jmedchem.4c01122","article-title":"An Update\non the Nitrogen Heterocycle Compositions and Properties of U.S. FDA-Approved\nPharmaceuticals (2013\u20132023)","volume":"67","author":"Marshall","year":"2024","journal-title":"J. Med.\nChem."},{"issue":"38","key":"2026091609115244500_cit50","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202405186","article-title":"A General Photoactive H-Bonding EDA Complex Model Drives the Selective\nHydrothiolation and Hydroxysulfenylation of Carbonyl Activated Alkenes","volume":"63","author":"Yan","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"issue":"24","key":"2026091609115244500_cit51","doi-asserted-by":"publisher","first-page":"4011","DOI":"10.1002\/ejoc.200900139","article-title":"Palladium-Catalysed\nCross-Coupling and Related Processes:\nSome Interesting Observations That Have Been Exploited in Synthetic\nChemistry","volume":"2009","author":"McGlacken","year":"2009","journal-title":"Eur. J. Org. Chem."},{"issue":"40","key":"2026091609115244500_cit52","doi-asserted-by":"publisher","first-page":"36053","DOI":"10.1021\/jacs.5c10599","article-title":"Use of\nElectron-Transfer Mediators to Access Higher\nElectrochemical Current Densities in Ni-Catalyzed Cross-Electrophile\nCoupling","volume":"147","author":"Zhu","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"2","key":"2026091609115244500_cit53","doi-asserted-by":"publisher","first-page":"566","DOI":"10.1039\/D2CS00706A","article-title":"Cyclic Voltammetry\nand Chronoamperometry: Mechanistic\nTools for Organic Electrosynthesis","volume":"53","author":"Rafiee","year":"2024","journal-title":"Chem. Soc.\nRev."},{"issue":"12","key":"2026091609115244500_cit54","doi-asserted-by":"publisher","first-page":"2036","DOI":"10.1038\/s41557-024-01627-5","article-title":"Zinc and Manganese Redox Potentials\nin Organic Solvents and Their Influence on Nickel-Catalysed Cross-Electrophile\nCoupling","volume":"16","author":"Su","year":"2024","journal-title":"Nat. Chem."},{"issue":"51","key":"2026091609115244500_cit55","doi-asserted-by":"publisher","first-page":"35275","DOI":"10.1021\/jacs.4c12581","article-title":"Selective Ni(I)\/Ni(III) Process for\nConsecutive Geminal C(Sp3)\u2013C(Sp2) Bond\nFormation","volume":"146","author":"Li","year":"2024","journal-title":"J. Am. Chem. 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