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Herein, we report a cyclopropenimine-enabled copper-catalyzed radical cyclization that addresses this challenge. A range of 3,3-disubstituted oxindoles bearing a quaternary carbon center at the C3 position, including those incorporating aryl substituents, was obtained in good yields under mild conditions. Mechanistic investigations, including radical trapping, EPR, kinetic isotope effect experiments, cyclic voltammetry, and DFT studies, reveal that productive catalysis arises from a balance between oxidative C\u2013X bond activation and reductive catalyst regeneration. The phenylene-bridged cyclopropenimine scaffold effectively modulates the redox behavior of the copper center, thereby enabling efficient reactions of tertiary alkyl halides, including chlorides. These findings highlight how the structural features of the cyclopropenimine scaffold regulate competing redox processes within a catalytic cycle and provide a foundation for future radical transformations involving challenging alkyl electrophiles.<\/jats:p>","DOI":"10.1021\/jacs.6c09015","type":"journal-article","created":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T21:16:31Z","timestamp":1785791791000},"page":"34560-34568","source":"Crossref","is-referenced-by-count":0,"title":["Cyclopropenimine-Enabled\nRedox Control in Copper-Catalyzed\nRadical Cyclization to 3,3-Disubstituted Oxindoles"],"prefix":"10.1021","volume":"148","author":[{"given":"Sarah","family":"Jang","sequence":"first","affiliation":[{"name":"KAIST , , 291 Daehak-ro , Yuseong-gu, ,","place":["Daejeon, Republic of Korea, 34141"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Seongryeol","family":"Jeung","sequence":"additional","affiliation":[{"name":"Yonsei University , , ,","place":["Seoul, Republic of Korea, 03722"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sumin","family":"Kim","sequence":"additional","affiliation":[{"name":"KAIST , , 291 Daehak-ro , Yuseong-gu, ,","place":["Daejeon, Republic of Korea, 34141"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4531-9392","authenticated-orcid":true,"given":"Sarah Yunmi","family":"Lee","sequence":"additional","affiliation":[{"name":"KAIST , , 291 Daehak-ro , Yuseong-gu, ,","place":["Daejeon, Republic of Korea, 34141"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,3]]},"reference":[{"key":"2026081910250975500_cit1a","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2021.111842","article-title":"Oxindole and Its Derivatives: A Review on Recent Progress\nin Biological Activities","volume":"141","author":"Khetmalis","year":"2021","journal-title":"Biomed. 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