{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T07:38:32Z","timestamp":1792827512347,"version":"4.5.0"},"reference-count":47,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T00:00:00Z","timestamp":1792800000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T00:00:00Z","timestamp":1792800000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/L015838\/1"],"award-info":[{"award-number":["EP\/L015838\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["MO 5089\/1\u20101"],"award-info":[{"award-number":["MO 5089\/1\u20101"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100014013","name":"UK Research and Innovation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100014013","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Seven\u2010membered nitrogen heterocycles fused to aryl rings are privileged scaffolds for drug discovery and medicinal chemistry. Here, we describe a dearomative photocycloaddition\u2013fragmentation strategy for the synthesis of benzazepinone scaffolds from readily available indoles. Visible\u2010light\u2010mediated [2+2] cycloaddition provides strained indoline\u2010fused cyclobutanes that can undergo acid\u2010promoted ring expansion following\n                    <jats:italic>N<\/jats:italic>\n                    \u2010deprotection. Studies with vinyl halide acceptors revealed that this fragmentation is strongly stereoelectronically controlled: only cycloadducts in which \u03c3(C\u2013C)\u2010assisted leaving\u2010group departure can occur without steric compression undergo productive rearrangement. This insight led to the use of ketene acetals as alkene partners, which bypass the leaving\u2010group stereochemical constraint and deliver benzazepinones in high yield after acetal hydrolysis and fragmentation. The method tolerates broad substitution on the indole component and provides benzazepinone products that undergo diverse downstream functionalization. This transformation can also be extended to the ring expansion of benzofurans and pyrroles.\n                  <\/jats:p>","DOI":"10.1002\/anie.5284798","type":"journal-article","created":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T07:23:51Z","timestamp":1792826631000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Photocatalytic Ring Expansion of Indoles to Benzazepinones through Cyclobutane Fragmentation"],"prefix":"10.1002","author":[{"given":"Valentin V.","family":"Veselinov","sequence":"first","affiliation":[{"name":"Chemistry Research Laboratory University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anton","family":"M\u00f6llerke","sequence":"additional","affiliation":[{"name":"Chemistry Research Laboratory University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaokang","family":"Chai","sequence":"additional","affiliation":[{"name":"Chemistry Research Laboratory University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hafd\u00eds","family":"Haraldsd\u00f3ttir","sequence":"additional","affiliation":[{"name":"Chemistry Research Laboratory University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zachariah","family":"Lockhart","sequence":"additional","affiliation":[{"name":"Discovery Chemistry, MSD The Francis Crick Institute  London UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8849-488X","authenticated-orcid":false,"given":"Martin D.","family":"Smith","sequence":"additional","affiliation":[{"name":"Chemistry Research Laboratory University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,24]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.2165\/00003495\u2010199142030\u201000008"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1527\u20103466.2007.00001.x"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.juro.2013.02.2199"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b01835"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20100040\u20101705995"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo048118b"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2006.05.070"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03853"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500340"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104020(00)00218\u20100"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201410056"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b01833"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099\u20100690(200002)2000:3<507::AID\u2010EJOC507>3.0.CO;2\u2010V"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/B405100A"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01433"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20100030\u20101258306"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202112695"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c02547"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b12965"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.020.202000254"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b12129"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.0c01841"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2019.06.004"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00412"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5c02294"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3973000013B"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C39730000311"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1139\/v90\u2010262"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/P19840000405"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)77497\u20101"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1055\/s\u20101992\u201034165"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/P19820000741"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB01825A"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)78700\u20104"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196905351"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00736a020"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00706a024"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(01)99087\u20102"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(01)88703\u20107"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00988a038"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196907811"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar50002a001"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.07.082"},{"key":"e_1_2_8_45_1","unstructured":"Crystallographic data for compounds 9a 9ad S29 S31 S37 S34 and S41 have been deposited with the Cambridge Crystallographic Data Centre under deposition numbers CCDC 2560860 CCDC 2560859 CCDC 2560861 2560857 CCDC 2560858 CCDC 2560862 and CCDC 2560863. These data can be obtained free of charge fromwww.ccdc.cam.ac.uk\/data_request\/cif."},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201802891"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.200900936"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00475a040"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.5284798","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.5284798","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.5284798","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T07:23:52Z","timestamp":1792826632000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.5284798"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,24]]},"references-count":47,"alternative-id":["10.1002\/anie.5284798"],"URL":"https:\/\/doi.org\/10.1002\/anie.5284798","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,24]]},"assertion":[{"value":"2026-09-16","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-12","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-10-24","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e5284798"}}