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Redox-neutral 1,2-dicarbofunctionalization is equally effective. Oxidative hetero-1,2-dicarbofunctionalization of alkenes, utilizing two different nucleophiles, is unprecedented, despite its potential to generate two C(sp3) centers in a single step. This constraint is mostly due to the formation of several byproducts, including the homocoupling of oxidatively generated alkyl radicals. The direct use of abundant natural functional groups, such as carboxylic acids, in organic synthesis is particularly appealing. Nonetheless, they are utilized in 1,2-dicarbofunctionalization in the form of redox-active esters alongside other coupling partners. Here, we demonstrate the heterocoupling of two distinct nucleophiles by applying the concept of the persistent radical effect. The approach utilizes unprotected alkyl carboxylic acids to produce two successive C(sp3) centers, including quaternary centers. Studies involving radical trapping, binding energy, and DFT calculations corroborate the hypothesized mechanism.<\/jats:p>","DOI":"10.1021\/jacs.5c21411","type":"journal-article","created":{"date-parts":[[2026,6,4]],"date-time":"2026-06-04T12:18:49Z","timestamp":1780575529000},"page":"23577-23584","source":"Crossref","is-referenced-by-count":3,"title":["Oxidative\nHetero-Coupling: Iron- and Copper-Mediated\n1,2-Dicarbofunctionalization"],"prefix":"10.1021","volume":"148","author":[{"given":"Chandru","family":"Murugan","sequence":"first","affiliation":[{"name":"Indian Institute of Science Education and Research Thiruvananthapuram , , Vithura, , ,","place":["Thiruvananthapuram, Kerala, India, 695551"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bincy","family":"Chindan","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Thiruvananthapuram , , Vithura, , ,","place":["Thiruvananthapuram, Kerala, India, 695551"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sanjai R.","family":"Yogaraj","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Thiruvananthapuram , , Vithura, , ,","place":["Thiruvananthapuram, Kerala, India, 695551"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sheryl C.","family":"Parakkal","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Thiruvananthapuram , , Vithura, , ,","place":["Thiruvananthapuram, Kerala, India, 695551"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Venkadesh","family":"Balakrishnan","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Thiruvananthapuram , , Vithura, , ,","place":["Thiruvananthapuram, Kerala, India, 695551"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3209-3315","authenticated-orcid":true,"given":"Ramesh","family":"Rasappan","sequence":"additional","affiliation":[{"name":"Indian Institute of Science Education and Research Thiruvananthapuram , , Vithura, , ,","place":["Thiruvananthapuram, Kerala, India, 695551"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,6,4]]},"reference":[{"key":"2026073023092257000_cit1a","doi-asserted-by":"publisher","first-page":"2277","DOI":"10.1002\/asia.201800647","article-title":"Transition-metal-catalyzed\nthree-component difunctionalizations of alkenes","volume":"13","author":"Zhang","year":"2018","journal-title":"Chem.\u2013Asian J."},{"key":"2026073023092257000_cit1b","doi-asserted-by":"publisher","first-page":"3013","DOI":"10.1021\/acs.joc.7b03128","article-title":"Strategies toward dicarbofunctionalization\nof unactivated olefins by combined Heck carbometalation and cross-coupling","volume":"83","author":"Giri","year":"2018","journal-title":"J. Org. Chem."},{"key":"2026073023092257000_cit1c","doi-asserted-by":"publisher","first-page":"3415","DOI":"10.1021\/acs.accounts.1c00329","article-title":"Transition metal (Ni, Cu, Pd)-catalyzed alkene dicarbofunctionalization\nreactions","volume":"54","author":"Wickham","year":"2021","journal-title":"Acc. Chem. Res."},{"key":"2026073023092257000_cit2a","doi-asserted-by":"publisher","first-page":"9189","DOI":"10.1039\/D1SC02547C","article-title":"Photoinduced 1,2-dicarbofunctionalization\nof alkenes with organotrifluoroborate nucleophilesviaradical\/polar\ncrossover","volume":"12","author":"Cabrera-Afonso","year":"2021","journal-title":"Chem. Sci."},{"key":"2026073023092257000_cit2b","doi-asserted-by":"publisher","first-page":"14073","DOI":"10.1021\/jacs.9b07194","article-title":"N-Heterocyclic\ncarbene-catalyzed radical relay enabling vicinal alkylacylation of\nalkenes","volume":"141","author":"Ishii","year":"2019","journal-title":"J. Am. Chem. 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Chem."},{"key":"2026073023092257000_cit5d","doi-asserted-by":"publisher","first-page":"12816","DOI":"10.1039\/C8CC07587E","article-title":"Alkylarylation of styrenes via direct C(sp3)\u2013Br\/C(sp2)-H functionalization mediated by photoredox and copper cooperative\ncatalysis","volume":"54","author":"Yong","year":"2018","journal-title":"Chem. Commun."},{"key":"2026073023092257000_cit5e","doi-asserted-by":"publisher","first-page":"236","DOI":"10.1021\/acscatal.8b04191","article-title":"Visible-light-mediated deaminative three-component\ndicarbofunctionalization of styrenes with benzylic radicals","volume":"9","author":"Klauck","year":"2019","journal-title":"ACS Catal."},{"key":"2026073023092257000_cit5f","doi-asserted-by":"publisher","first-page":"10333","DOI":"10.1038\/s41467-024-54170-9","article-title":"Ligand-enabled Ni-catalysed\ndicarbofunctionalisation of alkenes with diverse native functional\ngroups","volume":"15","author":"Wang","year":"2024","journal-title":"Nat. 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