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Here we report a photoinduced nickel-catalyzed strategy for the regio- and cross-selective 1,2-dialkylation of activated alkenes, including electron-poor olefins and styrenes, in which a methyl group and a second alkyl fragment are installed at defined, complementary positions across the C\u2550C bond. The process relies on iodine(III) carboxylates, either preformed or generated in situ from the corresponding carboxylic acids, as alkyl-radical precursors, enabling the concurrent formation of a methyl radical and a second alkyl radical under the same reaction conditions. Selectivity arises from a radical-sorting process in which a Ni(II) catalyst captures a methyl radical to generate a high-valent Ni\u2013Me intermediate, while the second alkyl radical undergoes Giese-type addition to the activated alkene, followed by SH2 C(sp3)\u2013C(sp3) coupling to deliver the cross-dialkylated product. The method accommodates secondary and tertiary alkyl radicals and, importantly, also differentiates methyl from primary alkyl radicals, with broad functional group tolerance and compatibility with complex molecules. Mechanistic experiments support this radical-sorting model. Finally, chiral auxiliary-substituted alkenes enable highly diastereoselective variants, extending this radical sorting strategy to the synthesis of enantioenriched products.<\/jats:p>","DOI":"10.1021\/jacs.6c09101","type":"journal-article","created":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T16:02:04Z","timestamp":1786204924000},"page":"34569-34578","source":"Crossref","is-referenced-by-count":0,"title":["Methyl-Selective Radical\nSorting for the Regio- and\nStereoselective Dialkylation of Activated Alkenes"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3803-6159","authenticated-orcid":true,"given":"Binlin","family":"Zhao","sequence":"first","affiliation":[{"name":"Nanjing Forestry University , , ,","place":["Nanjing, China, 210037"]},{"name":"Nanjing University , , ,","place":["Nanjing, China, 210093"]},{"name":"University of Bologna , , ,","place":["Bologna, Italy, 40129"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wen","family":"Liu","sequence":"additional","affiliation":[{"name":"Nanjing Forestry University , , ,","place":["Nanjing, China, 210037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Changping","family":"Fang","sequence":"additional","affiliation":[{"name":"Nanjing Forestry University , , ,","place":["Nanjing, China, 210037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Su","family":"Huang","sequence":"additional","affiliation":[{"name":"University of Bologna , , ,","place":["Bologna, Italy, 40129"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mai","family":"Zhang","sequence":"additional","affiliation":[{"name":"Nanjing Forestry University , , ,","place":["Nanjing, China, 210037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liting","family":"Du","sequence":"additional","affiliation":[{"name":"Nanjing Forestry University , , ,","place":["Nanjing, China, 210037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9629-6464","authenticated-orcid":true,"given":"Mengtao","family":"Ma","sequence":"additional","affiliation":[{"name":"Nanjing Forestry University , , ,","place":["Nanjing, China, 210037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8722-4602","authenticated-orcid":true,"given":"Paolo","family":"Melchiorre","sequence":"additional","affiliation":[{"name":"University of Bologna , , ,","place":["Bologna, Italy, 40129"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,8]]},"reference":[{"key":"2026081910245444100_cit1a","doi-asserted-by":"publisher","first-page":"6726","DOI":"10.1039\/D5CS00181A","article-title":"Navigating\nthe functionalization of unactivated alkenes via visible\nlight photocatalysis","volume":"54","author":"Cao","year":"2025","journal-title":"Chem. 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Res."},{"key":"2026081910245444100_cit2b","doi-asserted-by":"publisher","first-page":"1036","DOI":"10.1038\/s44160-025-00860-1","article-title":"Iron-catalysed\nradical difunctionalization of alkenes","volume":"4","author":"Gogoi","year":"2025","journal-title":"Nat.\nSynth."},{"key":"2026081910245444100_cit2c","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2025.134656","article-title":"Recent advances in directing group-free\n1,2-dialkylation of alkenes","volume":"180","author":"Wang","year":"2025","journal-title":"Tetrahedron"},{"key":"2026081910245444100_cit2d","doi-asserted-by":"publisher","first-page":"1701","DOI":"10.6023\/cjoc202312020","article-title":"Recent Progress in Radical Involved\nAlkene Dialkylation","volume":"44","author":"Lu","year":"2024","journal-title":"Chin. J. Org. 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Chem."},{"key":"2026081910245444100_cit14","doi-asserted-by":"publisher","first-page":"23351","DOI":"10.1021\/jacs.5c07367","article-title":"Radical\nSorting Catalysis via Bimolecular Homolytic\nSubstitution (SH2): Opportunities for C(sp3)\u2013C(sp3) Cross-Coupling Reactions","volume":"147","author":"McWhinnie","year":"2025","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081910245444100_cit15a","doi-asserted-by":"publisher","first-page":"104","DOI":"10.1038\/s41586-024-07165-x","article-title":"Alkene\ndialkylation by triple radical sorting","volume":"628","author":"Wang","year":"2024","journal-title":"Nature"},{"key":"2026081910245444100_cit15b","doi-asserted-by":"publisher","first-page":"10274","DOI":"10.1021\/jacs.4c02284","article-title":"A Bimolecular Homolytic Substitution-Enabled Platform\nfor Multicomponent Cross-Coupling of Unactivated Alkenes","volume":"146","author":"Cong","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026081910245444100_cit16","doi-asserted-by":"publisher","first-page":"2296","DOI":"10.1021\/jacs.4c14965","article-title":"Aminoalkylation\nof Alkenes Enabled by Triple Radical Sorting","volume":"147","author":"Lyon","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026081910245444100_cit17","doi-asserted-by":"publisher","first-page":"15693","DOI":"10.1021\/jacs.4c05744","article-title":"Triple\nRadical Sorting: Aryl-Alkylation of Alkenes","volume":"146","author":"Wang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026081910245444100_cit18","doi-asserted-by":"publisher","first-page":"23435","DOI":"10.1021\/jacs.6c03814","article-title":"Oxyalkylation of Alkenes via Triple Radical Sorting","volume":"148","author":"Harstad","year":"2026","journal-title":"J. Am. Chem. 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Chem., Int. Ed."},{"key":"2026081910245444100_cit20","doi-asserted-by":"publisher","first-page":"3481","DOI":"10.1021\/acs.accounts.2c00607","article-title":"Carboxylic\nAcids as Adaptive Functional Groups in Metallaphotoredox Catalysis","volume":"55","author":"Beil","year":"2022","journal-title":"Acc. Chem. Res."},{"key":"2026081910245444100_cit21","doi-asserted-by":"publisher","first-page":"2683","DOI":"10.1021\/ja00007a049","article-title":"Rates of decarboxylation of acyloxy\nradicals formed\nin the photocleavage of substituted 1-naphthylmethyl alkanoates","volume":"113","author":"Hilborn","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"2026081910245444100_cit22","doi-asserted-by":"publisher","first-page":"21278","DOI":"10.1021\/jacs.2c08989","article-title":"Nickel Catalysis via SH2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling\nof Aliphatic Acids","volume":"144","author":"Tsymbal","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026081910245444100_cit23","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202524825","article-title":"50 Years of\nGiese Reaction \u2013 a Personal View","volume":"65","author":"Spichty","year":"2026","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026081910245444100_cit24a","doi-asserted-by":"publisher","first-page":"753","DOI":"10.1002\/anie.198307531","article-title":"Formation of C-C Bonds by Addition\nof Free Radicals to Alkenes","volume":"22","author":"Giese","year":"1983","journal-title":"Angew. Chem., Int.\nEd. Engl."},{"key":"2026081910245444100_cit24b","doi-asserted-by":"publisher","first-page":"1340","DOI":"10.1002\/1521-3773(20010417)40:8&lt;1340::AID-ANIE1340&gt;3.0.CO;2-#","article-title":"Factors Controlling\nthe Addition of Carbon-Centered Radicals to Alkenes\u2500An Experimental\nand Theoretical Perspective","volume":"40","author":"Fischer","year":"2001","journal-title":"Angew. Chem., Int.\nEd. Engl."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c09101","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/32\/34569\/66465146\/jacs.6c09101.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/32\/34569\/66465146\/jacs.6c09101.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T14:45:52Z","timestamp":1787150752000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/32\/34569\/5250711\/Methyl-Selective-Radical-Sorting-for-the-Regio-and"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,8]]},"references-count":48,"journal-issue":{"issue":"32","published-online":{"date-parts":[[2026,8,8]]},"published-print":{"date-parts":[[2026,8,19]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c09101","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,8]]}}}