{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T03:59:10Z","timestamp":1792814350993,"version":"4.5.0"},"reference-count":75,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2024,7,25]],"date-time":"2024-07-25T00:00:00Z","timestamp":1721865600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/100019180","name":"HORIZON EUROPE European Research Council","doi-asserted-by":"publisher","award":["OLECAT, Grant ID 833540"],"award-info":[{"award-number":["OLECAT, Grant ID 833540"]}],"id":[{"id":"10.13039\/100019180","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2024,8,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We report a photochemical method for the semipinacol rearrangement of unactivated allylic alcohols. Aliphatic as well as aromatic groups participate as migrating groups, yielding a variety of \u03b1,\u03b1\u2010disubstituted ketones. The reaction proceeds under mild conditions and is compatible with ethers, esters, halides, nitriles, carbamates, and substituted arenes. The operationally simple and fully catalytic conditions prescribe 1\u2005mol\u2009% benzothiazinoquinoxaline as organophotocatalyst, 0.5\u2005mol\u2009% Co\u2010salen, and 10\u2005mol\u2009% lutidinium triflate and, importantly, display reactivity complementary to procedures employing Br\u00f8nsted acid. We showcase the utility of the protocol in late\u2010stage drug diversifications.<\/jats:p>","DOI":"10.1002\/anie.202407827","type":"journal-article","created":{"date-parts":[[2024,6,7]],"date-time":"2024-06-07T13:18:33Z","timestamp":1717766313000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":48,"title":["Cobalt\u2010Catalyzed Photo\u2010Semipinacol Rearrangement of Unactivated Allylic Alcohols"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9251-2887","authenticated-orcid":false,"given":"Henry","family":"Lindner","sequence":"first","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog-Weg 3 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1472-490X","authenticated-orcid":false,"given":"Erick M.","family":"Carreira","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Applied Biosciences ETH Z\u00fcrich  Vladimir-Prelog-Weg 3 8093 Z\u00fcrich Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,7,25]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00003a005"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr4001385"},{"key":"e_1_2_3_4_1","unstructured":"\u00a0"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19144050202"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-08-052349-1.00077-9"},{"key":"e_1_2_3_7_1","unstructured":"\u00a0"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/CS9720100073"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-08-052349-1.00045-7"},{"key":"e_1_2_3_10_1","unstructured":"\u00a0"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197600091"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610382"},{"key":"e_1_2_3_13_1","unstructured":"\u00a0"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)78044-0"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19270600539"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00396a071"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19830660803"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00308a001"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.05.019"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068434l"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-021-1188-x"},{"key":"e_1_2_3_22_1","unstructured":"\u00a0"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503062"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja074678r"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101256v"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr5001496"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aao5894"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201703556"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315759"},{"key":"e_1_2_3_30_1","unstructured":"\u00a0"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00057"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01449"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4031616"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b09671"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00602"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-30395-4"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3QO01929B"},{"key":"e_1_2_3_38_1","unstructured":"\u00a0"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC02386A"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200055g"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/b505707h"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906291n"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC48547A"},{"key":"e_1_2_3_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01302a023"},{"key":"e_1_2_3_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c02960"},{"key":"e_1_2_3_46_1","unstructured":"\u00a0"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b12075"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b10645"},{"key":"e_1_2_3_49_2","unstructured":"During the final stages of this work we became aware of work involving semipinacol rearrangements on a preprint server (C. Teskey D. Lunic N. Vystavkin Research Square 2024 DOI:10.21203\/rs.3.rs-3888384\/v1). The study reports 1 2-migration of exclusively aryl groups under photo-cobalt dual-catalysis. Importantly the reaction prescribes the use of Hantzsch ester (0.8\u2005equiv) AcOH (1.0\u2005equiv) and HFIP (9.5\u2005equiv) as reagents in benzene (0.03\u2005M)."},{"key":"e_1_2_3_50_1","unstructured":"\u00a0"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202319515"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c00527"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202200229"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-20872-z"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202100221"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.2c05109"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202304882"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202214433"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202310639"},{"key":"e_1_2_3_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c10989"},{"key":"e_1_2_3_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c10133"},{"key":"e_1_2_3_62_1","unstructured":"No epoxidation product was observed in the1H NMR spectrum of the unpurified reaction mixture."},{"key":"e_1_2_3_63_1","unstructured":"\u00a0"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC02250A"},{"key":"e_1_2_3_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c11680"},{"key":"e_1_2_3_66_1","unstructured":"\u00a0"},{"key":"e_1_2_3_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00334"},{"key":"e_1_2_3_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04112B"},{"key":"e_1_2_3_69_1","unstructured":"\u00a0"},{"key":"e_1_2_3_70_2","author":"Wilson C. V.","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_3_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c02128"},{"key":"e_1_2_3_72_1","unstructured":"There is uncertainty on the nature of the substitution of the organocobalt intermediate and whether it proceeds directly from the electrophilic [CoIV]-alkyl intermediate or the corresponding carbocation. Our work does not differentiate between these two options."},{"key":"e_1_2_3_73_1","unstructured":"\u00a0"},{"key":"e_1_2_3_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA20007A"},{"key":"e_1_2_3_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302673"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202407827","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,8,19]],"date-time":"2024-08-19T01:44:22Z","timestamp":1724031862000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202407827"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,25]]},"references-count":75,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2024,8,26]]}},"alternative-id":["10.1002\/anie.202407827"],"URL":"https:\/\/doi.org\/10.1002\/anie.202407827","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,7,25]]},"assertion":[{"value":"2024-04-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-07-25","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202407827"}}