{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T22:55:17Z","timestamp":1791413717367,"version":"4.3.3"},"reference-count":70,"publisher":"Wiley","issue":"40","license":[{"start":{"date-parts":[[2025,8,11]],"date-time":"2025-08-11T00:00:00Z","timestamp":1754870400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2025,9,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The Wacker oxidation is a powerful synthetic method widely employed for the transformation of monosubstituted alkenes into methyl ketones. Its substrate scope has progressively expanded to include internal disubstituted and, more recently,\n                    <jats:italic>gem<\/jats:italic>\n                    \u2010disubstituted alkenes. Herein, we report the first examples of Wacker\u2010type oxidation of trisubstituted alkenes under Pd(II)\/Pd(IV) catalysis. In the presence of Selectfluor (2.3 equiv) and a catalytic amount of Pd(MeCN)\n                    <jats:sub>4<\/jats:sub>\n                    (BF\n                    <jats:sub>4<\/jats:sub>\n                    )\n                    <jats:sub>2<\/jats:sub>\n                    (10 mol%), exocyclic trisubstituted\n                    <jats:italic>\u03b1<\/jats:italic>\n                    ,\n                    <jats:italic>\u03b2<\/jats:italic>\n                    \u2010unsaturated carbonyl compounds undergo a fluorinative one\u2010carbon ring expansion to deliver 2\u2010fluoro\u20101,3\u2010dicarbonyl compounds in good yields. The reaction displays broad functional group tolerance, including alkyl halide, aryl halide, alkyl tosylate, hydroxyl, carboxylic acid, ester, secondary amide, ketone, cyano, and\n                    <jats:italic>N<\/jats:italic>\n                    \u2010phthalimide. While a semi\u2010pinacol rearrangement of the Pd(IV) intermediate is a plausible mechanistic pathway given the excellent nucleofugality of the Pd(IV) atom, preliminary studies suggest that a 1,2\u2010alkyl\/Pd(IV) dyotropic rearrangement is operative in product formation.\n                  <\/jats:p>","DOI":"10.1002\/anie.202511478","type":"journal-article","created":{"date-parts":[[2025,8,12]],"date-time":"2025-08-12T06:53:20Z","timestamp":1754981600000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Wacker Oxidation of Trisubstituted Alkenes: Pd(II)\u2010Catalyzed Oxidative Ring Expansion of Exocyclic\n                    <i>\u03b1,\u03b2<\/i>\n                    \u2010Unsaturated Carbonyl to 2\u2010Fluoro\u20101,3\u2010Dicarbonyl Compounds"],"prefix":"10.1002","volume":"64","author":[{"given":"Vincent","family":"Go\u00eblo","sequence":"first","affiliation":[{"name":"Laboratory of Synthesis and Natural Products (LSPN) Institute of Chemical Sciences and Engineering Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne EPFL\u2010SB\u2010ISIC\u2010LSPN  BCH 5304 Lausanne 1015 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qian","family":"Wang","sequence":"additional","affiliation":[{"name":"Laboratory of Synthesis and Natural Products (LSPN) Institute of Chemical Sciences and Engineering Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne EPFL\u2010SB\u2010ISIC\u2010LSPN  BCH 5304 Lausanne 1015 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jieping","family":"Zhu","sequence":"additional","affiliation":[{"name":"Laboratory of Synthesis and Natural Products (LSPN) Institute of Chemical Sciences and Engineering Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne EPFL\u2010SB\u2010ISIC\u2010LSPN  BCH 5304 Lausanne 1015 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,8,11]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19590710503"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196200801"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903992"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902194"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404070"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1984-30848"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CY01820A"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404856"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)87430-4"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/b103066n"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja902591g"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905184"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo302638v"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209541"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201404712"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00344"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1980.257"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39770000583"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202215381"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adg3182"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.64.2578"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00789a030"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00960a002"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00956a019"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.06.029"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00698-y"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c06578"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211470"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c06158"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202316393"},{"key":"e_1_2_6_31_1","first-page":"11061","volume":"146","author":"Delcaillau T.","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c07706"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c13359"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c15764"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c01108"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00381"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C39940000343"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1139(97)00127-9"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540130905"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.3c07367"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja711029u"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja900213d"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408650"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-021-00574-5"},{"key":"e_1_2_6_45_1","unstructured":"Deposition numbers CCDC 2391722 (2f\u20102) 2391108 (2p) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02422"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol052100l"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB01825G"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b12877"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01657"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja061706h"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9003242"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202105490"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0347444"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201105235"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00102a005"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c05050"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02628"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB00035B"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2021.132113"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC00113F"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200600579"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm0495982"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202103943"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/0960-894X(95)00459-7"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202100301"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol051569d"},{"key":"e_1_2_6_68_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2013.07.004"},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol9003405"},{"key":"e_1_2_6_70_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(76)80130-5"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202511478","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T12:08:58Z","timestamp":1760443738000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202511478"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,8,11]]},"references-count":70,"journal-issue":{"issue":"40","published-print":{"date-parts":[[2025,9,26]]}},"alternative-id":["10.1002\/anie.202511478"],"URL":"https:\/\/doi.org\/10.1002\/anie.202511478","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,8,11]]},"assertion":[{"value":"2025-05-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-08-04","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-08-11","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202511478"}}