{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T15:03:36Z","timestamp":1789743816132,"version":"4.0.1"},"reference-count":43,"publisher":"American Chemical Society (ACS)","issue":"37","license":[{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22478356"],"award-info":[{"award-number":["22478356"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22578415"],"award-info":[{"award-number":["22578415"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["W2512071"],"award-info":[{"award-number":["W2512071"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008327","name":"Zhejiang University of Technology","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008327","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Zhejiang Key Laboratory of Green Manufacturing Technology for the Chemical Drugs","award":["2025ZY01073"],"award-info":[{"award-number":["2025ZY01073"]}]},{"name":"Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,18]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Herein, we report a photoredox\/nickel dual-catalyzed strategy that merges the deconstruction of cyclic alcohols with low-valent metal oxidative addition, enabling the direct use of carboxylic acids as acyl donors for the programmable synthesis of 1,n-diketones, ranging from 1,4- to 1,7-diketones. The method accommodates both aliphatic and aromatic acids, and the resulting 1,n-diketones serve as versatile handles for downstream heterocyclization. Its synthetic utility is demonstrated by the late-stage functionalization of natural products and the efficient construction of bioactive molecules.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03098","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T16:29:07Z","timestamp":1788452947000},"page":"11546-11551","source":"Crossref","is-referenced-by-count":0,"title":["Metallaphotoredox-Catalyzed\nDeconstructive Acylation\nof Cycloalkanols with Carboxylic Acids to Access Remote Diketones"],"prefix":"10.1021","volume":"28","author":[{"given":"Jiayin","family":"Wang","sequence":"first","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, P. R. China, 310014"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinyao","family":"Hu","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, P. R. China, 310014"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Siyu","family":"Pan","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, P. R. China, 310014"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bin","family":"Sun","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, P. R. China, 310014"]},{"name":"Key Laboratory for Green Pharmaceutical Technology and Equipment (Zhejiang University of Technology) of Ministry of Education , , , ,","place":["Deqing, Zhejiang, P. R. China, 313200"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1997-6209","authenticated-orcid":true,"given":"Can","family":"Jin","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, P. R. China, 310014"]},{"name":"Key Laboratory for Green Pharmaceutical Technology and Equipment (Zhejiang University of Technology) of Ministry of Education , , , ,","place":["Deqing, Zhejiang, P. R. China, 313200"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,2]]},"reference":[{"key":"2026091809423515000_cit1","doi-asserted-by":"publisher","first-page":"56","DOI":"10.1021\/acs.jnatprod.1c00649","article-title":"Phytochemical Investigation of the\nRoots of Ipomoea Asarifolia and Antiproliferative Activity of the\nIsolated Compounds against Multiple Myeloma Cells","volume":"85","author":"Saraux","year":"2022","journal-title":"J. Nat. Prod."},{"key":"2026091809423515000_cit2","doi-asserted-by":"publisher","first-page":"171","DOI":"10.1021\/acs.jnatprod.7b00806","article-title":"The Chemistry\nof\nSome Dalodesmidean Millipedes from Tasmania (Diplopoda, Polydesmida)","volume":"81","author":"Jones","year":"2018","journal-title":"J. Nat. Prod."},{"key":"2026091809423515000_cit3","doi-asserted-by":"publisher","first-page":"5398","DOI":"10.1021\/acscatal.6c00215","article-title":"Carbonylative Synthesis of 1,4-Diketones","volume":"16","author":"Wang","year":"2026","journal-title":"ACS\nCatal."},{"key":"2026091809423515000_cit4","doi-asserted-by":"publisher","first-page":"21078","DOI":"10.1021\/acsomega.9b02473","article-title":"Combinatorial\nEnzymatic Synthesis of Unnatural Long-Chain \u03b2-Branch\nPyrones by a Highly Promiscuous Enzyme","volume":"4","author":"Pan","year":"2019","journal-title":"ACS\nOmega"},{"key":"2026091809423515000_cit5","doi-asserted-by":"publisher","first-page":"219","DOI":"10.1016\/j.jlumin.2017.01.019","article-title":"Spectroscopic Properties\nof Diketopyrrolopyrrole Derivatives with Long Alkyl Chains","volume":"185","author":"Barszcz","year":"2017","journal-title":"J. Lumin."},{"key":"2026091809423515000_cit6","doi-asserted-by":"publisher","first-page":"108271","DOI":"10.1016\/j.cclet.2023.108271","article-title":"Modular Synthesis\nof 1,4-Diketones through Regioselective Bis-Acylation of Olefins by\nMerging NHC and Photoredox Catalysis","volume":"34","author":"Li","year":"2023","journal-title":"Chin.\nChem. Lett."},{"key":"2026091809423515000_cit7","doi-asserted-by":"publisher","first-page":"1213","DOI":"10.1002\/anie.201810798","article-title":"Stereocontrolled\nSynthesis of 1,4-Dicarbonyl Compounds by Photochemical Organocatalytic\nAcyl Radical Addition to Enals","volume":"58","author":"Goti","year":"2019","journal-title":"Angew. Chem.\nInt. Ed."},{"key":"2026091809423515000_cit8","doi-asserted-by":"publisher","first-page":"2854","DOI":"10.1021\/acs.orglett.0c00967","article-title":"Rhodium-Catalyzed Room Temperature\nC-C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones","volume":"22","author":"Pati","year":"2020","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit9","doi-asserted-by":"publisher","first-page":"5101","DOI":"10.1021\/acs.orglett.9b01703","article-title":"Manganese-Catalyzed\nRing-Opening Coupling Reactions of Cyclopropanols with Enones","volume":"21","author":"Zhang","year":"2019","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit10","doi-asserted-by":"publisher","first-page":"24734","DOI":"10.1021\/jacs.5c06232","article-title":"Distal\nC(sp3)\u2013H\nAmidation via Ind*RhIII Catalyzed Nitrene Transfer","volume":"147","author":"Ross","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026091809423515000_cit11","doi-asserted-by":"publisher","first-page":"1198","DOI":"10.1038\/s41929-025-01435-1","article-title":"Photobiocatalytic Radical Repositioning\nfor Enantioselective Acylation of Remote C\u2013C\/C\u2013H Bonds","volume":"8","author":"Ming","year":"2025","journal-title":"Nat. Catal."},{"key":"2026091809423515000_cit12","doi-asserted-by":"publisher","first-page":"17693","DOI":"10.1002\/anie.202105977","article-title":"Asymmetric Alkoxy- and Hydroxy-Carbonylations of Functionalized\nAlkenes Assisted by \u03b2-Carbonyl Groups","volume":"60","author":"Ren","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026091809423515000_cit13","doi-asserted-by":"publisher","first-page":"900","DOI":"10.1038\/s41929-024-01194-5","article-title":"Remote Site-Selective\nArene C\u2013H Functionalization Enabled by N-Heterocyclic Carbene\nOrganocatalysis","volume":"7","author":"Li","year":"2024","journal-title":"Nat. Catal."},{"key":"2026091809423515000_cit14","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202421476","article-title":"Stereoselective\nSynthesis of 1,n-Dicarbonyl Compounds Through Palladium-Catalyzed\nRing\nOpening\/Isomerization of Densely Substituted Cyclopropanols","volume":"64","author":"Teschers","year":"2025","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026091809423515000_cit15","doi-asserted-by":"publisher","first-page":"7202","DOI":"10.1021\/acs.orglett.6c01624","article-title":"Ring-Opening of Nonstrained Cyclic Carboxylic Acid\nInduced Carbo-Carbonylation of Alkenes To Construct Asymmetric Long-Chain\nDiketones","volume":"28","author":"Li","year":"2026","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit16","doi-asserted-by":"publisher","first-page":"1695","DOI":"10.1021\/acs.orglett.2c00326","article-title":"Photoredox\nOrganocatalysis for the Enantioselective Synthesis of 1,7-Dicarbonyl\nCompounds","volume":"24","author":"Wong","year":"2022","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit17","doi-asserted-by":"publisher","first-page":"13175","DOI":"10.1039\/D3CC04765B","article-title":"NHC-Catalyzed\nRadical Acylation of Cycloalkyl Silyl Peroxides to Access 1,6-, 1,7-,\nand 1,8-Diketones","volume":"59","author":"Liu","year":"2023","journal-title":"Chem. Commun."},{"key":"2026091809423515000_cit18","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202507542","article-title":"Deconstructive\nRadical\u2013Radical\nCoupling for Programmable Remote Acylation","volume":"64","author":"Cao","year":"2025","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026091809423515000_cit19","doi-asserted-by":"publisher","first-page":"6726","DOI":"10.1021\/jacs.9b02238","article-title":"A Radical\nApproach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and\nAmines","volume":"141","author":"Ni","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"2026091809423515000_cit20","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202506424","article-title":"Enantioselective Decarboxylative\nAcylation of \u03b1-Hydroxy Acids\nwith Carboxylic Acids via Photoredox\/Nickel Dual Catalysis","volume":"64","author":"Deng","year":"2025","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026091809423515000_cit21","doi-asserted-by":"publisher","first-page":"125","DOI":"10.1038\/s41467-023-35800-0","article-title":"Site- and\nEnantioselective Cross-Coupling of Saturated N-Heterocycles with Carboxylic\nAcids by Cooperative Ni\/Photoredox Catalysis","volume":"14","author":"Shu","year":"2023","journal-title":"Nat. Commun."},{"key":"2026091809423515000_cit22","doi-asserted-by":"publisher","first-page":"202614","DOI":"10.70401\/cc.2026.0025","article-title":"Catalytic\nEnantioselective Construction of Saturated (Hetero)Cycles via Radical\nCross-Coupling","volume":"2","author":"Luo","year":"2026","journal-title":"Chiral Chem."},{"key":"2026091809423515000_cit23","doi-asserted-by":"publisher","first-page":"19058","DOI":"10.1021\/jacs.0c10471","article-title":"Direct Enantioselective\nC(sp3)\u2013H Acylation for the Synthesis of \u03b1-Amino\nKetones","volume":"142","author":"Shu","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026091809423515000_cit24","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202213739","article-title":"Selective Cross-Ketonization\nof Carboxylic Acids Enabled\nby Metallaphotoredox Catalysis","volume":"61","author":"Whyte","year":"2022","journal-title":"Angew. Chem.\nInt. Ed."},{"key":"2026091809423515000_cit25","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202518424","article-title":"Iridium Photosensitizers Immobilized on Metal\u2013Organic\nLayers Lead to Enhanced Enantioselectivity in Ni\/Ir Dual Photocatalysis","volume":"64","author":"Peng","year":"2025","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026091809423515000_cit26","doi-asserted-by":"publisher","first-page":"11414","DOI":"10.1039\/D1SC03596G","article-title":"Synthesis of C-Acyl Furanosides via\nthe Cross-Coupling of Glycosyl Esters with Carboxylic Acids","volume":"12","author":"Wei","year":"2021","journal-title":"Chem. Sci."},{"key":"2026091809423515000_cit27","doi-asserted-by":"publisher","first-page":"4040","DOI":"10.1002\/anie.201511438","article-title":"Direct Acylation of C(sp3)\u2013H Bonds\nEnabled by Nickel and Photoredox Catalysis","volume":"55","author":"Joe","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026091809423515000_cit28","doi-asserted-by":"publisher","first-page":"3612","DOI":"10.1021\/acs.orglett.7b01588","article-title":"Direct Conversion of Carboxylic Acids to Alkyl Ketones","volume":"19","author":"Amani","year":"2017","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit29","doi-asserted-by":"publisher","first-page":"11938","DOI":"10.1021\/jacs.5b08304","article-title":"Fragment Couplings via CO2 Extrusion\u2013Recombination:\nExpansion of a Classic Bond-Forming Strategy via Metallaphotoredox","volume":"137","author":"Le","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026091809423515000_cit30","doi-asserted-by":"publisher","first-page":"1457","DOI":"10.1021\/jacs.8b12552","article-title":"A Redox Strategy\nfor Light-Driven, Out-of-Equilibrium Isomerizations and Application\nto Catalytic C-C Bond Cleavage Reactions","volume":"141","author":"Ota","year":"2019","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026091809423515000_cit31","doi-asserted-by":"publisher","first-page":"11124","DOI":"10.1039\/D0SC04542J","article-title":"Catalytic Generation of Alkoxy Radicals\nfrom Unfunctionalized Alcohols","volume":"11","author":"Tsui","year":"2020","journal-title":"Chem. Sci."},{"key":"2026091809423515000_cit32","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1021\/acs.chemrev.0c00346","article-title":"Selective\nCarbon-Carbon Bond Cleavage of Cyclopropanols","volume":"121","author":"McDonald","year":"2021","journal-title":"Chem. Rev."},{"key":"2026091809423515000_cit33","doi-asserted-by":"publisher","first-page":"3553","DOI":"10.1021\/acs.orglett.6c00432","article-title":"CuCl-Promoted \u03b2-Acylation of Cyclopropanols with\nThioesters","volume":"28","author":"Ponomarev","year":"2026","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit34","doi-asserted-by":"publisher","first-page":"1780","DOI":"10.1021\/ol400666x","article-title":"C -Acylation of Cyclopropanols: Preparation\nof Functionalized 1,4-Diketones","volume":"15","author":"Parida","year":"2013","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit35","doi-asserted-by":"publisher","first-page":"2368","DOI":"10.1039\/C9CC00378A","article-title":"Visible-Light-Induced\nConsecutive C\u2013C Bond Fragmentation\nand Formation for the Synthesis of Elusive Unsymmetric 1,8-Dicarbonyl\nCompounds","volume":"55","author":"Ji","year":"2019","journal-title":"Chem. Commun."},{"key":"2026091809423515000_cit36","doi-asserted-by":"publisher","first-page":"2179","DOI":"10.1039\/C8DT04689A","article-title":"O\u2013H and (CO)N\u2013H Bond\nWeakening by Coordination to Fe(II)","volume":"48","author":"Resa","year":"2019","journal-title":"Dalton\nTrans."},{"key":"2026091809423515000_cit37","doi-asserted-by":"publisher","first-page":"10392","DOI":"10.1039\/D3CC02888G","article-title":"Palladium-Catalyzed Coupling of Amides\nand Cyclopropanols for the Synthesis of \u03b3-Diketones","volume":"59","author":"Fang","year":"2023","journal-title":"Chem. Commun."},{"key":"2026091809423515000_cit38","doi-asserted-by":"publisher","first-page":"7972","DOI":"10.1021\/acscatal.6c01346","article-title":"Redox-Neutral\nRadical\u2013Polar Crossover [3+2] Annulation of Cyclopropanols\nand Alkenes","volume":"16","author":"Yamamoto","year":"2026","journal-title":"ACS Catal."},{"key":"2026091809423515000_cit39","doi-asserted-by":"publisher","first-page":"720","DOI":"10.1007\/BF00568950","article-title":"Formation\nof Nitrogen Heterocycles in the Hydroamination of 1,5-Diketones","volume":"18","author":"Kharchenko","year":"1982","journal-title":"Chem. Heterocycl. Compd."},{"key":"2026091809423515000_cit40","doi-asserted-by":"publisher","first-page":"7075","DOI":"10.1016\/j.bmc.2006.07.006","article-title":"Synthesis and Trypanocidal\nActivity of 1,4-Bis-(3,4,5-Trimethoxy-Phenyl)-1,4-Butanediol and 1,4-Bis-(3,4-Dimethoxyphenyl)-1,4-Butanediol","volume":"14","author":"Bernardes","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"2026091809423515000_cit41","doi-asserted-by":"publisher","first-page":"8646","DOI":"10.1039\/D3OB01465G","article-title":"Electrochemical\nChemoselective Hydrogenation of 1,4-Enediones\nwith HFIP as the Hydrogen Donor: Scalable Access to 1,4-Diketones","volume":"21","author":"Li","year":"2023","journal-title":"Org. Biomol. Chem."},{"key":"2026091809423515000_cit42","doi-asserted-by":"publisher","first-page":"7219","DOI":"10.1021\/acs.orglett.0c02514","article-title":"Aryl Pyrazoles\nfrom Photocatalytic Cycloadditions of Arenediazonium","volume":"22","author":"Cardinale","year":"2020","journal-title":"Org. Lett."},{"key":"2026091809423515000_cit43","doi-asserted-by":"publisher","first-page":"91","DOI":"10.1002\/adsc.202300939","article-title":"Ring-Opening Coupling Reaction of Cyclopropanols with\nElectrophilic Alkenes Enabled by Decatungstate as Photoredox Catalyst","volume":"366","author":"Krech","year":"2024","journal-title":"Adv. Synth. Catal."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c03098","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/37\/11546\/68209126\/acs.orglett.6c03098.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/37\/11546\/68209126\/acs.orglett.6c03098.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T14:12:04Z","timestamp":1789740724000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/37\/11546\/5405825\/Metallaphotoredox-Catalyzed-Deconstructive"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,2]]},"references-count":43,"journal-issue":{"issue":"37","published-online":{"date-parts":[[2026,9,2]]},"published-print":{"date-parts":[[2026,9,18]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c03098","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,2]]}}}