{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T19:46:12Z","timestamp":1785527172114,"version":"3.56.0"},"reference-count":46,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2026,6,20]],"date-time":"2026-06-20T00:00:00Z","timestamp":1781913600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,6,20]],"date-time":"2026-06-20T00:00:00Z","timestamp":1781913600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100007234","name":"University of Chicago","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007234","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R01GM109054"],"award-info":[{"award-number":["R01GM109054"]}],"id":[{"id":"10.13039\/100000057","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":[[2026,8,3]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>The insertion of five\u2010membered heteroarenes into the C\u2500C bonds of benzocyclobutenones (BCBs) has been achieved. This process proceeds under mild conditions and does not require the use of a transition metal catalyst. A variety of fused polycyclic compounds based on indoles, 7\u2010azaindoles, benzothiophenes, benzofurans, and thiophenes relevant to bioactive scaffolds are efficiently accessed through this approach. The reaction is scalable, and the products are suitable for various late\u2010stage derivatizations. Preliminary mechanistic studies reveal a catalytic role of base in facilitating C\u2500C bond cleavage to generate a reactive intermediate which likely engages in subsequent dearomative cycloaddition with heteroarenes.<\/jats:p>","DOI":"10.1002\/anie.6371423","type":"journal-article","created":{"date-parts":[[2026,6,20]],"date-time":"2026-06-20T09:09:47Z","timestamp":1781946587000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Transition Metal\u2010Free Heteroarene Insertion Into C\u2500C Bonds of Benzocyclobutenones"],"prefix":"10.1002","volume":"65","author":[{"given":"Cole J.","family":"Wagner","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Chicago  Chicago Illinois United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1331-6015","authenticated-orcid":false,"given":"Guangbin","family":"Dong","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Chicago  Chicago Illinois United States"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,6,20]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.2c00473"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-323-85153-4.00007-1"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c01011"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00825"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201909213"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527823086"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(01)86935\u20105"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199517211"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja050859m"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/B505392G"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2023.05.032"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja065868p"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202500148"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.3987\/REV-19-917"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.4c01122"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781118695692"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.4c00376"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2011.04.020"},{"key":"e_1_2_7_20_1","unstructured":"K.Kinoshita K.Asoh N.Furuichi et\u00a0al. Tetracyclic Compound (2015) US20150150845A1."},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.3987\/COM\u201092\u20106105"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.adi1606"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.4c00257"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.5c01122"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC00705E"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03210"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trechm.2019.12.002"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202771"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.2c00400"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c00063"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00138"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201603382"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC04359C"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00599"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00569"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b04691"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202106709"},{"key":"e_1_2_7_38_1","unstructured":"Deposition Number 2541836 (for 3r) Contains 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_7_39_1","unstructured":"Compared to indole benzofuran and benzothiophene preparation of the corresponding pyrrole and furan\u2010based bromoboronates is much more challenging."},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300390"},{"key":"e_1_2_7_41_1","unstructured":"The reaction can still afford high yield in dark or in the presence of TEMPO suggesting that a radical mechanism is unlikely."},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19980810207"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397910701575269"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202502894"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201310544"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5CC00609K"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b05111"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.6371423","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.6371423","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.6371423","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T18:09:38Z","timestamp":1785521378000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.6371423"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6,20]]},"references-count":46,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2026,8,3]]}},"alternative-id":["10.1002\/anie.6371423"],"URL":"https:\/\/doi.org\/10.1002\/anie.6371423","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,6,20]]},"assertion":[{"value":"2026-04-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-06-01","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-06-20","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e6371423"}}