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Herein, we report a copper\u2010catalyzed, photoinduced defluorinative C\u2212O coupling between trifluoromethylarenes and alcohols. This method allows for direct access to a wide selection of difluorobenzylether (ArCF\n                    <jats:sub>2<\/jats:sub>\n                    OR) molecules, including a compound displaying liquid crystal behavior. Through slight modification of the protocol, we were able to generate difluorobenzyliodide (ArCF\n                    <jats:sub>2<\/jats:sub>\n                    I) products, another class of synthetically useful fluorine\u2010bearing molecules. Mechanistic investigations first suggested that ArCF\n                    <jats:sub>2<\/jats:sub>\n                    I can serve as a reservoir to steadily supply the key ArCF\n                    <jats:sub>2<\/jats:sub>\n                    \u22c5 radical species. Furthermore, experimental evidence supported a mechanism consisting of two collaborative cycles: C\u2212F activation operated by a homoleptic Cu(I) coordinated by two bisphosphine ligands as the photocatalyst and C\u2212O coupling promoted by a Cu(I) ligated by a single bisphosphine ligand. The critical roles of the two salt additives, lithium iodide and zinc acetate, in orchestrating the two cycles were also elucidated. This dual\u2010role copper catalyst demonstrates the power of base metal photoredox catalysis in achieving both substrate activation and chemical bond formation via a single catalytic system.\n                  <\/jats:p>","DOI":"10.1002\/anie.202419591","type":"journal-article","created":{"date-parts":[[2025,1,2]],"date-time":"2025-01-02T02:34:01Z","timestamp":1735785241000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Defluorinative C\u2212O Coupling between Trifluoromethylarenes and Alcohols via Copper Photoredox Catalysis"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1641-2555","authenticated-orcid":false,"given":"Priya","family":"Saha","sequence":"first","affiliation":[{"name":"Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) Hokkaido University  Kita 21, Nishi 10, Kita-ku Sapporo Hokkaido 001\u20130021 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6199-8802","authenticated-orcid":false,"given":"Mingoo","family":"Jin","sequence":"additional","affiliation":[{"name":"Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) Hokkaido University  Kita 21, Nishi 10, Kita-ku Sapporo Hokkaido 001\u20130021 Japan"},{"name":"List Sustainable Digital Transformation Catalyst Collaboration Research Platform Institute for Chemical Reaction Design and Discovery (ICReDD List-PF) Hokkaido University  Kita 21, Nishi 10, Kita-ku Sapporo Hokkaido 001\u20130021 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2618-9668","authenticated-orcid":false,"given":"Dennis Chung\u2010Yang","family":"Huang","sequence":"additional","affiliation":[{"name":"Institute for Chemical Reaction Design and Discovery (WPI-ICReDD) Hokkaido University  Kita 21, Nishi 10, Kita-ku Sapporo Hokkaido 001\u20130021 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,1,22]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2023.101548"},{"key":"e_1_2_7_2_1","unstructured":"\u00a0"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201703602"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b08822"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CY02336K"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00057"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00018"},{"key":"e_1_2_7_9_1","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"crossref","unstructured":"S. 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