{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T13:45:14Z","timestamp":1792158314983,"version":"4.4.0"},"reference-count":42,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T00:00:00Z","timestamp":1790640000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2021YFC2102900"],"award-info":[{"award-number":["2021YFC2102900"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004731","name":"Natural Science Foundation of Zhejiang Province","doi-asserted-by":"publisher","award":["LMS26B020005"],"award-info":[{"award-number":["LMS26B020005"]}],"id":[{"id":"10.13039\/501100004731","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Central Guidance for Local Science and Technology Development Funds Project","award":["2026ZY01003"],"award-info":[{"award-number":["2026ZY01003"]}]},{"name":"Research Program of State Key Laboratory of Green Chemical Synthesis and Conversion","award":["SKLGSC-ZZ-202612"],"award-info":[{"award-number":["SKLGSC-ZZ-202612"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Direct methods for selective functionalization of C(sp3)\u2013H bonds could greatly streamline the synthesis of complex molecules. However, such transformations remain challenging. Herein, we report a cobalt-catalyzed azidation of benzylic C\u2013H bonds that enables efficient access to benzylic azides. The reaction employs the C\u2013H substrate as the limiting reagent and features broad substrate scope, as well as good functional-group tolerance. The key to success lies in the utilization of a commercially available N,N-ligand and cobalt catalyst. Preliminary mechanistic study indicates that hydrogen-atom transfer (HAT) of benzylic C\u2013H bonds affords a benzyl radical that is involved in the reaction process.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01153","type":"journal-article","created":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T09:02:34Z","timestamp":1790672554000},"page":"13603-13608","source":"Crossref","is-referenced-by-count":0,"title":["Cobalt-Catalyzed\nAzidation\nof Benzylic C\u2013H\nBonds"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-6886-1090","authenticated-orcid":true,"given":"Peng-Fei","family":"Wang","sequence":"first","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]},{"name":"Zhejiang Key Laboratory of Green Manufacturing Technology for Chemical Drugs , , ,","place":["Deqing, Zhejiang, China, 313200"]},{"name":"Key Laboratory for Green Pharmaceutical Technology and Equipment (Zhejiang University of Technology) of Ministry of Education , , ,","place":["Deqing, Zhejiang, China, 313200"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiang","family":"Wang","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan-Qing","family":"Zeng","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bing-Fa","family":"Xiang","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Li-Hua","family":"Zhao","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jing","family":"Chen","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-8136-1535","authenticated-orcid":true,"given":"Xian-Heng","family":"Song","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2284-0882","authenticated-orcid":true,"given":"Ya-Jun","family":"Wang","sequence":"additional","affiliation":[{"name":"Zhejiang University of Technology , , , ,","place":["Hangzhou, Zhejiang, China, 310032"]},{"name":"Zhejiang Key Laboratory of Green Manufacturing Technology for Chemical Drugs , , ,","place":["Deqing, Zhejiang, China, 313200"]},{"name":"Key Laboratory for Green Pharmaceutical Technology and Equipment (Zhejiang University of Technology) of Ministry of Education , , ,","place":["Deqing, Zhejiang, China, 313200"]},{"name":"State Key Laboratory of Green Chemical Synthesis and Conversion , , ,","place":["Deqing, Zhejiang, China, 313200"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,29]]},"reference":[{"key":"2026101608080201700_cit1a","doi-asserted-by":"publisher","first-page":"86","DOI":"10.1016\/j.gresc.2020.07.001","article-title":"Radical azidation\nas a means of constructing C(sp3)-N3 bonds","volume":"1","author":"Ge","year":"2020","journal-title":"Green Synth. Catal."},{"key":"2026101608080201700_cit1b","doi-asserted-by":"publisher","first-page":"4253","DOI":"10.1021\/acs.chemrev.0c01124","article-title":"New Strategies for the Synthesis\nof Aliphatic Azides","volume":"121","author":"Sivaguru","year":"2021","journal-title":"Chem. Rev."},{"key":"2026101608080201700_cit2a","doi-asserted-by":"publisher","first-page":"523","DOI":"10.1016\/j.tet.2006.09.048","article-title":"The Aza-Wittig Reaction: An Efficient\nTool for the\nConstruction of Carbon-Nitrogen Double Bonds","volume":"63","author":"Palacios","year":"2007","journal-title":"Tetrahedron"},{"key":"2026101608080201700_cit2b","doi-asserted-by":"publisher","first-page":"2577","DOI":"10.3762\/bjoc.12.253","article-title":"Catalytic Wittig\nand Aza-Wittig Reactions","volume":"12","author":"Lao","year":"2016","journal-title":"Beilstein J. Org.\nChem."},{"key":"2026101608080201700_cit3","doi-asserted-by":"publisher","first-page":"3023","DOI":"10.1002\/cber.189002302232","article-title":"Ueber Stickstoffwasserstoffsau\u0308re\n(Azoimid) N3H","volume":"23","author":"Curtius","year":"1890","journal-title":"Ber. Dtsch. Chem.\nGes."},{"key":"2026101608080201700_cit4a","doi-asserted-by":"publisher","first-page":"2004","DOI":"10.1002\/1521-3773(20010601)40:11&lt;2004::AID-ANIE2004&gt;3.0.CO;2-5","article-title":"Click Chemistry:\nDiverse Chemical Function from a Few Good Reactions","volume":"40","author":"Kolb","year":"2001","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101608080201700_cit4b","doi-asserted-by":"crossref","DOI":"10.1002\/9783527694174","volume-title":"Click Reactions in Organic Synthesis","author":"Chandrasekaran","year":"2016"},{"key":"2026101608080201700_cit5a","doi-asserted-by":"publisher","first-page":"1040","DOI":"10.1021\/acs.accounts.5b00020","article-title":"Transition-Metal-Catalyzed\nC-N Bond Forming Reactions Using Organic Azides as the Nitrogen Source:\nA Journey for the Mild and Versatile C-H Amination","volume":"48","author":"Shin","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"2026101608080201700_cit5b","doi-asserted-by":"publisher","first-page":"117","DOI":"10.1002\/tcr.201300027","article-title":"Asymmetric Nitrene Transfer Reactions: Sulfimidation,\nAziridination and C-H Amination Using Azide Compounds as Nitrene Precursors","volume":"14","author":"Uchida","year":"2014","journal-title":"Chem. Rec."},{"key":"2026101608080201700_cit5c","doi-asserted-by":"publisher","first-page":"4301","DOI":"10.1021\/acs.chemrev.9b00665","article-title":"The Staudinger\nLigation","volume":"120","author":"Bednarek","year":"2020","journal-title":"Chem. Rev."},{"key":"2026101608080201700_cit5d","doi-asserted-by":"publisher","first-page":"4840","DOI":"10.1039\/c0cs00123f","article-title":"Bioconjugation via Azide-Staudinger Ligation: An Overview","volume":"40","author":"Schilling","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"2026101608080201700_cit6a","doi-asserted-by":"publisher","first-page":"546","DOI":"10.1039\/C5CS00628G","article-title":"The medicinal chemist\u2019s toolbox\nfor late stage functionalization of drug-like molecules","volume":"45","author":"Cernak","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"2026101608080201700_cit6b","doi-asserted-by":"publisher","first-page":"3175","DOI":"10.1016\/j.chempr.2022.10.005","article-title":"Selective functionalization of benzylic\nC(sp3)\u2013H bonds to synthesize complex molecules","volume":"8","author":"Zhang","year":"2022","journal-title":"Chem"},{"key":"2026101608080201700_cit7a","doi-asserted-by":"publisher","first-page":"100603","DOI":"10.1016\/j.checat.2023.100603","article-title":"Photochemical iron-catalyzed decarboxylative\nazidation via the merger of ligand-to-metal charge transfer and radical\nligand transfer catalysis","volume":"3","author":"Kao","year":"2023","journal-title":"Chem. Catal."},{"key":"2026101608080201700_cit7b","doi-asserted-by":"publisher","first-page":"1912","DOI":"10.1002\/ange.201309991","article-title":"Copper-Catalyzed Intermolecular Trifluoromethylazidation of Alkenes:\nConvenient Access to CF3-Containing Alkyl azides","volume":"126","author":"Wang","year":"2014","journal-title":"Angew. Chem., Int. Ed."},{"issue":"16","key":"2026101608080201700_cit16c","doi-asserted-by":"publisher","first-page":"4340","DOI":"10.1021\/ol5021477","article-title":"Photoredox-Induced\nThree-Component Azido- and Aminotrifluoromethylation of Alkenes","volume":"16","author":"Dagousset","year":"2014","journal-title":"Org. Lett."},{"issue":"9","key":"2026101608080201700_cit7d","doi-asserted-by":"publisher","first-page":"833","DOI":"10.1002\/cjoc.201400167","article-title":"Copper-Catalyzed Three-Component Azidotrifluoromethylation\/Difunctionalization\nof Alkenes","volume":"32","author":"Yang","year":"2014","journal-title":"Chin. J. Chem."},{"issue":"16","key":"2026101608080201700_cit8a","doi-asserted-by":"publisher","first-page":"4077","DOI":"10.1002\/chem.201806288","article-title":"Double Cu-Catalyzed Direct Csp3\u2013H Azidation\/CuAAC Reaction: A Direct Approach towards\nDemanding Triazole Conjugates","volume":"25","author":"Tobias Brandhofer","year":"2019","journal-title":"Chem. Eur. J."},{"key":"2026101608080201700_cit8b","doi-asserted-by":"publisher","first-page":"11885","DOI":"10.1021\/acs.joc.9b01742","article-title":"Copper-Catalyzed Regioselective sp3 C\u2013H\nAzidation of Alkyl Substituents of Indoles and Tetrahydrocarbazoles","volume":"84","author":"Huang","year":"2019","journal-title":"J. Org. Chem."},{"key":"2026101608080201700_cit8c","doi-asserted-by":"publisher","first-page":"11388","DOI":"10.1021\/jacs.0c05362","article-title":"Site-Selective Copper-Catalyzed Azidation of Benzylic\nC\u2013H Bonds","volume":"142","author":"Suh","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026101608080201700_cit9a","doi-asserted-by":"publisher","first-page":"5356","DOI":"10.1021\/ja402082p","article-title":"Enantioselective\nIron-Catalyzed Azidation of \u03b2-Keto Esters and\nOxindoles","volume":"135","author":"Deng","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"2026101608080201700_cit9b","doi-asserted-by":"publisher","first-page":"715","DOI":"10.1021\/acscentsci.6b00214","article-title":"Late Stage Azidation\nof Complex Molecules","volume":"2","author":"Karimov","year":"2016","journal-title":"ACS Cent. Sci."},{"key":"2026101608080201700_cit9c","doi-asserted-by":"publisher","first-page":"16184","DOI":"10.1021\/jacs.1c07330","article-title":"Mechanistic Investigation of the Iron-Catalyzed Azidation\nof Alkyl C(sp3)\u2013H Bonds with Zhdankin\u2019s \u03bb3-Azidoiodane","volume":"143","author":"Day","year":"2021","journal-title":"J. Am. Chem. Soc."},{"issue":"3","key":"2026101608080201700_cit9d","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.202400004","article-title":"Benzylic C(sp3)\u2013H azidation: copper vs iron catalysis","volume":"107","author":"Renteri\u0301a-Go\u0301mez","year":"2024","journal-title":"Helv. Chim. Acta"},{"key":"2026101608080201700_cit10a","doi-asserted-by":"publisher","first-page":"5300","DOI":"10.1021\/jacs.5b01983","article-title":"Manganese-Catalyzed\nLate-Stage Aliphatic C\u2013H Azidation","volume":"137","author":"Huang","year":"2015","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026101608080201700_cit10b","doi-asserted-by":"publisher","first-page":"17693","DOI":"10.1021\/jacs.0c08437","article-title":"Manganese-Catalyzed\nOxidative Azidation of C(sp3)\u2013H Bonds under Electrophotocatalytic\nConditions","volume":"142","author":"Niu","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026101608080201700_cit10c","doi-asserted-by":"publisher","first-page":"15383","DOI":"10.1021\/jacs.2c07089","article-title":"Site- and Enantioselective Manganese-Catalyzed Benzylic C\u2013H\nAzidation of Indolines","volume":"144","author":"Cao","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026101608080201700_cit11","doi-asserted-by":"publisher","first-page":"1646","DOI":"10.1021\/acs.orglett.6b00512","article-title":"Benzylic C\u2013H\nAzidation Using the Zhdankin Reagent and a Copper Photoredox Catalyst","volume":"18","author":"Rabet","year":"2016","journal-title":"Org. Lett."},{"issue":"8","key":"2026101608080201700_cit12a","doi-asserted-by":"publisher","first-page":"2890","DOI":"10.1039\/D0SC05924B","article-title":"Mangana( iii \/ iv )electro-catalyzed C(sp 3)\u2013H azidation","volume":"12","author":"Meyer","year":"2021","journal-title":"Chem. Sci."},{"key":"2026101608080201700_cit12b","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202201041","article-title":"A Facile Electrochemical\nStrategy for the Azidation of Benzylic C(sp3)\u2013H\nBonds","volume":"2022","author":"He","year":"2022","journal-title":"Eur. J. Org. Chem."},{"key":"2026101608080201700_cit13","doi-asserted-by":"publisher","first-page":"5373","DOI":"10.1021\/acs.orglett.5c01241","article-title":"A Metal-Free Oxidative Azidation Method for Selective Azidation of\nC(sp3)\u2013H Bonds and Diazidation of Alkenes","volume":"27","author":"Bai","year":"2025","journal-title":"Org. Lett."},{"issue":"3","key":"2026101608080201700_cit14","doi-asserted-by":"publisher","first-page":"537","DOI":"10.31635\/ccschem.023.202303412","article-title":"Recent Advances\nin Mn, Fe, Co, and Ni-Catalyzed Organic\nReactions","volume":"6","author":"Li","year":"2024","journal-title":"CCS Chem."},{"key":"2026101608080201700_cit15a","doi-asserted-by":"publisher","first-page":"1640","DOI":"10.1039\/D1CS00727K","article-title":"Copper-catalyzed\nradical relay in C(sp3)\u2013H functionalization","volume":"51","author":"Zhang","year":"2022","journal-title":"Chem. Soc. Rev."},{"issue":"17","key":"2026101608080201700_cit15b","doi-asserted-by":"publisher","first-page":"10192","DOI":"10.1021\/acs.chemrev.4c00188","article-title":"Strategies and Mechanisms\nof First-Row Transition Metal-Regulated Radical C\u2013H Functionalization","volume":"124","author":"Wang","year":"2024","journal-title":"Chem. Rev."},{"key":"2026101608080201700_cit16a","doi-asserted-by":"publisher","first-page":"1435","DOI":"10.1021\/cr9000786","article-title":"Cobalt-Catalyzed Cross-Coupling\nReactions","volume":"110","author":"Cahiez","year":"2010","journal-title":"Chem. Rev."},{"key":"2026101608080201700_cit16b","doi-asserted-by":"publisher","first-page":"1351","DOI":"10.1021\/acs.accounts.0c00238","article-title":"Cobalt-Catalyzed Cross-Couplings\nbetween Alkyl Halides and Grignard Reagents","volume":"53","author":"Gue\u0301rinot","year":"2020","journal-title":"Acc. Chem. Res."},{"key":"2026101608080201700_cit17","doi-asserted-by":"publisher","first-page":"1130","DOI":"10.31635\/ccschem.024.202303678","article-title":"Recent Advances in Cobalt-Catalyzed\nRegio- or Stereoselective\nHydrofunctionalization of Alkenes and Alkynes","volume":"6","author":"Li","year":"2024","journal-title":"CCS Chem."},{"key":"2026101608080201700_cit18","doi-asserted-by":"publisher","first-page":"2956","DOI":"10.1002\/cjoc.202200537","article-title":"Practical Synthesis of NFSI Derivatives\nthrough ArSO2NHF without F2","volume":"40","author":"Zhang","year":"2022","journal-title":"Chin. J. Chem."},{"key":"2026101608080201700_cit19a","doi-asserted-by":"publisher","first-page":"25","DOI":"10.1039\/a804291h","article-title":"Polarity-reversal catalysis of hydrogen-atom abstraction\nreactions: concepts and applications in organic chemistry","volume":"28","author":"Roberts","year":"1999","journal-title":"Chem. Soc. Rev."},{"key":"2026101608080201700_cit19b","doi-asserted-by":"publisher","first-page":"486","DOI":"10.1038\/s41570-021-00284-3","article-title":"Radical philicity and its role in\nselective organic transformations","volume":"5","author":"Parsaee","year":"2021","journal-title":"Nat. Rev.\nChem."},{"key":"2026101608080201700_cit19c","doi-asserted-by":"publisher","first-page":"682","DOI":"10.1038\/s44160-022-00108-2","article-title":"The interplay of polar effects in\ncontrolling the selectivity of radical reactions","volume":"1","author":"Ruffoni","year":"2022","journal-title":"Nat. Synth."},{"key":"2026101608080201700_cit19d","doi-asserted-by":"publisher","first-page":"28034","DOI":"10.1021\/jacs.4c06774","article-title":"Radical Polarity","volume":"146","author":"Garwood","year":"2024","journal-title":"J. Am. Chem.\nSoc"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01153","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/doi\/10.1021\/acs.joc.6c01153\/68685583\/acs.joc.6c01153.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/doi\/10.1021\/acs.joc.6c01153\/68685583\/acs.joc.6c01153.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T12:50:10Z","timestamp":1792155010000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/41\/13603\/5440464\/Cobalt-Catalyzed-Azidation-of-Benzylic-C-H-Bonds"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,29]]},"references-count":42,"journal-issue":{"issue":"41","published-online":{"date-parts":[[2026,9,29]]},"published-print":{"date-parts":[[2026,10,16]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01153","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,29]]}}}