{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T15:02:39Z","timestamp":1790348559175,"version":"4.1.0"},"reference-count":32,"publisher":"American Chemical Society (ACS)","issue":"38","license":[{"start":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T00:00:00Z","timestamp":1789171200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T00:00:00Z","timestamp":1789171200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T00:00:00Z","timestamp":1789171200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100013461","name":"Anhui Normal University","doi-asserted-by":"publisher","award":["114-022304"],"award-info":[{"award-number":["114-022304"]}],"id":[{"id":"10.13039\/501100013461","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22201011"],"award-info":[{"award-number":["22201011"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013314","name":"Higher Education Discipline Innovation Project","doi-asserted-by":"publisher","award":["D26004"],"award-info":[{"award-number":["D26004"]}],"id":[{"id":"10.13039\/501100013314","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Anhui Province","award":["2026LCX12"],"award-info":[{"award-number":["2026LCX12"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The development of transition-metal-catalyzed three-component C(sp3)\u2013H activation represents one of the most efficient strategies for the rapid construction of complex molecular architectures. Particularly, leveraging this strategy for the direct formation of dual C(sp3)\u2013C(sp3) bonds offers distinct advantages, whereas it remains largely challenging and underdeveloped. Herein, we report a rhodium-catalyzed three-component C(sp3)\u2013H activation of 8-methyl quinolines with diazo compounds and formaldehyde\/formaldimine. This protocol not only provides a novel route for the construction of dual C(sp3)\u2013C(sp3) bonds via a 1,1-addition process but also offers a convenient pathway to access a diverse array of 8-alkyl quinoline derivatives under mild conditions.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03300","type":"journal-article","created":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T16:02:35Z","timestamp":1789228955000},"page":"11925-11931","source":"Crossref","is-referenced-by-count":0,"title":["Rhodium-Catalyzed\nThree-Component C(sp3)\u2013H Activation of 8-Methyl\nQuinolines with Diazo Compounds\nand Formaldehyde\/Formaldimine to Access Dual C(sp3)\u2013C(sp3) Bonds"],"prefix":"10.1021","volume":"28","author":[{"given":"Jie-Ying","family":"Yang","sequence":"first","affiliation":[{"name":"Anhui Normal University , , ,","place":["Wuhu, China, 241002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin-Xin","family":"Shan","sequence":"additional","affiliation":[{"name":"Anhui Normal University , , ,","place":["Wuhu, China, 241002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ya-Ru","family":"Du","sequence":"additional","affiliation":[{"name":"Anhui Normal University , , ,","place":["Wuhu, China, 241002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuefei","family":"Hu","sequence":"additional","affiliation":[{"name":"Anhui Normal University , , ,","place":["Wuhu, China, 241002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2595-9803","authenticated-orcid":true,"given":"Kun","family":"An","sequence":"additional","affiliation":[{"name":"Anhui Normal University , , ,","place":["Wuhu, China, 241002"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1127-1944","authenticated-orcid":true,"given":"Zhong-Yuan","family":"Li","sequence":"additional","affiliation":[{"name":"Anhui Normal University , , ,","place":["Wuhu, China, 241002"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,12]]},"reference":[{"key":"2026092510103969300_cit1a","doi-asserted-by":"publisher","first-page":"8768","DOI":"10.1021\/acs.chemrev.6c00255","article-title":"Earth-Abundant 3d Transition Metal-Catalyzed Enantioselective\nC\u2013H Functionalization","volume":"126","author":"Qian","year":"2026","journal-title":"Chem. Rev."},{"key":"2026092510103969300_cit1b","doi-asserted-by":"publisher","first-page":"8925","DOI":"10.1039\/C8CS00716K","article-title":"Recent Applications\nof C\u2013H Functionalization in Complex Natural Product Synthesis","volume":"47","author":"Abrams","year":"2018","journal-title":"Chem. Soc. Rev."},{"key":"2026092510103969300_cit1c","doi-asserted-by":"publisher","first-page":"951","DOI":"10.1021\/acsmaterialslett.0c00206","article-title":"Recent Advances in C\u2013H Activation for the Synthesis of \u03c0-Extended\nMaterials","volume":"2","author":"Stepek","year":"2020","journal-title":"ACS Materials Lett."},{"key":"2026092510103969300_cit1d","doi-asserted-by":"publisher","first-page":"2910","DOI":"10.1021\/acs.accounts.5c00503","article-title":"From Mono-N-Protected Amino Acids to Pyridones:\nA Decade of Evolution of Bifunctional Ligands for Pd(II)-Catalyzed\nC\u2013H Activation","volume":"58","author":"Li","year":"2025","journal-title":"Acc. Chem. Res."},{"key":"2026092510103969300_cit1e","doi-asserted-by":"publisher","first-page":"10079","DOI":"10.1021\/acs.chemrev.3c00149","article-title":"Rhodium-Catalyzed\nAsymmetric C\u2013H Functionalization Reactions","volume":"123","author":"Liu","year":"2023","journal-title":"Chem. Rev."},{"key":"2026092510103969300_cit2","doi-asserted-by":"publisher","first-page":"6738","DOI":"10.1039\/D2CS00012A","article-title":"C\u2013H bond Activation and Sequential\nAddition\nto Two Different Coupling Partners: A Versatile Approach to Molecular\nXomplexity","volume":"51","author":"Brandes","year":"2022","journal-title":"Chem. Soc. Rev."},{"key":"2026092510103969300_cit3a","doi-asserted-by":"publisher","first-page":"4530","DOI":"10.1021\/jacs.1c12646","article-title":"Three-Component Coupling of Arenes, Ethylene, and Alkynes\nCatalyzed by a Cationic Bis(phosphine) Cobalt Complex: Intercepting\nMetallacyclopentenes for C\u2013H Functionalization","volume":"144","author":"Whitehurst","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510103969300_cit3b","doi-asserted-by":"publisher","first-page":"11938","DOI":"10.1021\/acscatal.1c03153","article-title":"Cobalt(III)-Catalyzed Diastereo- and Enantioselective\nThree-Component C\u2013H Functionalization","volume":"11","author":"Herraiz","year":"2021","journal-title":"ACS Catal."},{"key":"2026092510103969300_cit3c","doi-asserted-by":"publisher","first-page":"756","DOI":"10.1038\/s41929-019-0330-7","article-title":"\u03b1-Branched Amines by Catalytic 1,1-Addition of\nC\u2013H Bonds and Aminating Agents to Terminal Alkenes","volume":"2","author":"Maity","year":"2019","journal-title":"Nat. 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Chem."},{"key":"2026092510103969300_cit4a","doi-asserted-by":"publisher","first-page":"7648","DOI":"10.1021\/jacs.1c03492","article-title":"Use of Strain-Release\nfor the Diastereoselective Construction of Quaternary Carbon Centers","volume":"143","author":"Pinkert","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510103969300_cit4b","doi-asserted-by":"publisher","first-page":"10739","DOI":"10.1021\/acs.orglett.5c03345","article-title":"Three-Component\nReaction through Rh(III)-Catalyzed Strain Release of Bicyclo[1.1.0]butanes","volume":"27","author":"Dhal","year":"2025","journal-title":"Org. Lett."},{"key":"2026092510103969300_cit5a","doi-asserted-by":"publisher","first-page":"673","DOI":"10.1038\/s41929-018-0123-4","article-title":"Selective and Synergistic Cobalt(iii)-Catalysed\nThree-Component\nC\u2013H Bond Addition to Dienes and Aldehydes","volume":"1","author":"Boerth","year":"2018","journal-title":"Nat. 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Lett."},{"key":"2026092510103969300_cit6a","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202202364","article-title":"Stereoselective\nSynthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential\nC\u2013H Bond Addition to 1,3-Enynes and Aldehydes","volume":"61","author":"Xu","year":"2022","journal-title":"Angew. Chem., Int. 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Lett."},{"key":"2026092510103969300_cit7","doi-asserted-by":"publisher","first-page":"607","DOI":"10.1016\/j.chempr.2022.10.019","article-title":"Multicomponent Coupling\nand Macrocyclization Enabled by Rh(III)-Catalyzed Dual C\u2013H\nActivation: Macrocyclic Oxime Inhibitor of Influenza H1N1","volume":"9","author":"Wang","year":"2023","journal-title":"Chem"},{"key":"2026092510103969300_cit8","doi-asserted-by":"publisher","first-page":"5634","DOI":"10.1039\/D4CC00827H","article-title":"Rhodium-Catalyzed\nThree-Component C(sp3)\/C(sp2)\u2013H Activation\nEnabled by A Two-Fold Directing Group Strategy","volume":"60","author":"Hou","year":"2024","journal-title":"Chem. Commun."},{"key":"2026092510103969300_cit9","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202314395","article-title":"A Three-Component\nArene Difunctionalization: Merger of C(sp3)\/(sp2)\u2013H Bond Addition","volume":"62","author":"Ghosh","year":"2023","journal-title":"Angew. Chem., Int.\nEd."},{"key":"2026092510103969300_cit10a","doi-asserted-by":"publisher","first-page":"394","DOI":"10.1021\/acs.orglett.5c04827","article-title":"Construction of Chiral 1,2-Azaborines via Rhodium-Catalyzed Enantioselective\nCarbene N\u2013H Bond Insertion","volume":"28","author":"Zhang","year":"2026","journal-title":"Org. Lett."},{"key":"2026092510103969300_cit10b","doi-asserted-by":"publisher","first-page":"42","DOI":"10.1021\/jacs.7b10349","article-title":"Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C\u2013H Alkylation\nand Amidation Reactions of N-Phenoxyacetamides","volume":"140","author":"Wu","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510103969300_cit10c","doi-asserted-by":"publisher","first-page":"13513","DOI":"10.1021\/jacs.6c01890","article-title":"Chiral Isourea-Catalyzed Enantioselective Carbene Insertion\ninto an N\u2013H Bond through a Double Proton-Transfer Process","volume":"148","author":"Zhang","year":"2026","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510103969300_cit11a","doi-asserted-by":"publisher","first-page":"4131","DOI":"10.1039\/D1QO00551K","article-title":"Synthesis\nof 3-Spirooxindole 3H-Indoles through Rh(iii)-Catalyzed [4+1] Redox-Neutral\nSpirocyclization of N-Aryl Amidines with Diazo Oxindoles","volume":"8","author":"Zhou","year":"2021","journal-title":"Org. Chem. Front."},{"key":"2026092510103969300_cit11b","doi-asserted-by":"publisher","first-page":"7850","DOI":"10.1021\/acs.orglett.2c03288","article-title":"Rh(III)-Catalyzed Enaminone-Directed\nC\u2013H Coupling with Diazodicarbonyls for Skeleton-Divergent Synthesis\nof Isocoumarins and Naphthalenes","volume":"24","author":"Wu","year":"2022","journal-title":"Org. Lett."},{"key":"2026092510103969300_cit12","doi-asserted-by":"publisher","first-page":"2492","DOI":"10.1021\/ja411072a","article-title":"Mechanistic Studies of the Rhodium-Catalyzed\nDirect C\u2013H Amination\nReaction Using Azides as the Nitrogen Source","volume":"136","author":"Park","year":"2014","journal-title":"J. Am. Chem. Soc."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c03300","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/38\/11925\/68492447\/acs.orglett.6c03300.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/38\/11925\/68492447\/acs.orglett.6c03300.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T14:31:34Z","timestamp":1790346694000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/38\/11925\/5428929\/Rhodium-Catalyzed-Three-Component-C-sp3-H"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,12]]},"references-count":32,"journal-issue":{"issue":"38","published-online":{"date-parts":[[2026,9,12]]},"published-print":{"date-parts":[[2026,9,25]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c03300","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,12]]}}}