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The process of combining two carboxylic acids to furnish a ketone is termed ketonization. This is a potentially valuable transformation that has been underutilized in organic synthesis due to the harsh reaction conditions generally required and the lack of selectivity obtained when coupling two distinct carboxylic acids. We report herein a metallaphotoredox strategy that selectively generates unsymmetrical ketones via cross\u2010ketonization of two structurally dissimilar carboxylic acids. Cross\u2010selectivity is achieved by exploiting divergent reactivity of differentially substituted acids towards critical one\u2010 and two\u2010electron processes in the proposed coupling mechanism. This method is broadly applicable to a variety of functionalized carboxylic acids. It can also be applied to acids of similar steric profile by exploiting differences in their relative rates of decarboxylation.<\/jats:p>","DOI":"10.1002\/anie.202213739","type":"journal-article","created":{"date-parts":[[2022,11,1]],"date-time":"2022-11-01T12:38:40Z","timestamp":1667306320000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Selective Cross\u2010Ketonization of Carboxylic Acids Enabled by Metallaphotoredox Catalysis"],"prefix":"10.1002","volume":"61","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7261-4309","authenticated-orcid":false,"given":"Andrew","family":"Whyte","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Wisconsin-Madison  1101 University Avenue Madison WI 53706 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3934-4973","authenticated-orcid":false,"given":"Tehshik P.","family":"Yoon","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Wisconsin-Madison  1101 University Avenue Madison WI 53706 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,11,28]]},"reference":[{"key":"e_1_2_3_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CS00101B"},{"key":"e_1_2_3_2_1","unstructured":"\u00a0"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91316-4"},{"key":"e_1_2_3_4_2","first-page":"945","author":"Bram G.","year":"1964","journal-title":"Bull. 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