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Herein, we report the enantioselective acylation of benzylic C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2500H bond via a cooperative photoredox and N\u2010heterocyclic carbene (NHC) catalysis, affording the corresponding chiral \u03b1\u2010aryl ketones in moderate to good yields with good to excellent enantioselectivities (up to 99:1 er). The rational design of novel NHCs guided by the initial evaluation of available catalysts and their application promotes the asymmetric transformation. Mechanistic experiments and density functional theory (DFT) calculations support the formation of benzyl radical and ketyl radical intermediates and rationalize the coupling of these radical species via open\u2010shell singlet transition states to be the enantiodetermining step. This redox neutral protocol features mild conditions and is free of transition\u2010metals (TMs) and pre\u2010functionalized radical precursors.\n                  <\/jats:p>","DOI":"10.1002\/anie.202421151","type":"journal-article","created":{"date-parts":[[2025,3,11]],"date-time":"2025-03-11T19:38:46Z","timestamp":1741721926000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Enantioselective Acylation of Benzylic C(sp\n                    <sup>3<\/sup>\n                    )\u2212H Bond Enabled by a Cooperative Photoredox and N\u2010Heterocyclic Carbene Catalysis"],"prefix":"10.1002","volume":"64","author":[{"given":"Cao\u2010Bo","family":"Li","sequence":"first","affiliation":[{"name":"Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function CAS Research\/Education Center for Excellence in Molecular Sciences Institute of Chemistry, Chinese Academy of Sciences (CAS)  Beijing 100190 P.R. 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