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A chiral cobalt\u2010salen catalyst generates a highly electrophilic carbocation surrogate following hydrogen atom transfer and radical\u2013polar crossover steps. This methodology provides access to enantioenriched \u03b1\u2010aryl ketones through invertive displacement of a cobalt(IV) complex during 1,2\u2010aryl migration. A combination of readily available reagents, silane and\n                    <jats:italic>N<\/jats:italic>\n                    \u2010fluoropyridinium oxidant, are used to confer this type of reactivity. An exploration into the effect of aryl substitution revealed the reaction tolerates\n                    <jats:italic>para\u2010<\/jats:italic>\n                    and\n                    <jats:italic>meta\u2010<\/jats:italic>\n                    halogenated, mildly electron\u2010rich and electron\u2010poor aromatic rings with excellent enantioselectivities and yields. The yield of the rearrangement diminished with highly electron\u2010rich aryl rings whereas very electron\u2010deficient and\n                    <jats:italic>ortho<\/jats:italic>\n                    \u2010substituted arenes led to poor enantiocontrol. A Hammett analysis demonstrated the migratory preference for electron\u2010rich aromatic rings, which is consistent with the intermediacy of a phenonium cation.\n                  <\/jats:p>","DOI":"10.1002\/anie.202414342","type":"journal-article","created":{"date-parts":[[2024,9,23]],"date-time":"2024-09-23T13:43:48Z","timestamp":1727099028000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":38,"title":["Enantioselective Synthesis of \u03b1\u2010Aryl Ketones by a Cobalt\u2010Catalyzed Semipinacol Rearrangement"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6156-9776","authenticated-orcid":false,"given":"Panagiotis G.","family":"Kalomenopoulos","sequence":"first","affiliation":[{"name":"EaStCHEM School of Chemistry University of St Andrews  St Andrews Fife KY16 9ST UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2947-853X","authenticated-orcid":false,"given":"Balakumar","family":"Emayavaramban","sequence":"additional","affiliation":[{"name":"EaStCHEM School of Chemistry University of St Andrews  St Andrews Fife KY16 9ST UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2459-1872","authenticated-orcid":false,"given":"Craig P.","family":"Johnston","sequence":"additional","affiliation":[{"name":"EaStCHEM School of Chemistry University of St Andrews  St Andrews Fife KY16 9ST UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,6]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b04480"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903424"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1055\/a-1560-5245"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300621"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c13236"},{"key":"e_1_2_7_6_1","first-page":"24958","volume":"145","author":"Wang J.","year":"2023","journal-title":"J. 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