{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:30:49Z","timestamp":1786977049238,"version":"build-2736575974"},"reference-count":55,"publisher":"Wiley","issue":"32","license":[{"start":{"date-parts":[[2025,6,8]],"date-time":"2025-06-08T00:00:00Z","timestamp":1749340800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001711","name":"Schweizerischer Nationalfonds zur F\u00f6rderung der Wissenschaftlichen Forschung","doi-asserted-by":"publisher","award":["200020_212129"],"award-info":[{"award-number":["200020_212129"]}],"id":[{"id":"10.13039\/501100001711","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":[[2025,8,4]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Bicyclo[1.1.1]pentanes (BCPs) are well\u2010studied bioisosteres for\n                    <jats:italic>para<\/jats:italic>\n                    \u2010substituted benzene rings, and numerous methods for synthesizing 1,3\u2010difunctionalized BCPs have been developed. However, synthetic approaches to access vinyl BCP motifs remain limited, with only few reports on the synthesis of BCP\u2010olefins bearing heteroatom substituents. Herein, we present the synthesis of BCP\u2010substituted enamides, enol ethers, and vinyl sulfides through the sequential functionalization of ethynylbenziodoxolone (EBX) reagents containing a BCP scaffold. Stereoselective addition of a nucleophile generates heteroatomic Z\u2010vinylbenziodoxolone (VBX) reagents. The hypervalent iodine substituent of the VBX reagents serves then as a versatile platform for further arylation, vinylation, and trifluoromethylation. This method provides a modular synthesis of previously inaccessible heteroatom\u2010substituted vinyl BCPs.\n                  <\/jats:p>","DOI":"10.1002\/anie.202508404","type":"journal-article","created":{"date-parts":[[2025,5,28]],"date-time":"2025-05-28T06:10:12Z","timestamp":1748412612000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis of Bicyclo[1.1.1]Pentane Z\u2010Substituted Enamides, Enol Ethers, and Vinyl Sulfides Using Iodine (III) Reagents"],"prefix":"10.1002","volume":"64","author":[{"given":"Najung","family":"Lee","sequence":"first","affiliation":[{"name":"Laboratory of Catalysis and Organic Synthesis Institute of Chemical Sciences and Engineering, \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne  Lausanne CH\u20101015 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonas","family":"Dechent","sequence":"additional","affiliation":[{"name":"Laboratory of Catalysis and Organic Synthesis Institute of Chemical Sciences and Engineering, \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne  Lausanne CH\u20101015 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5268-5660","authenticated-orcid":false,"given":"Elija","family":"Grinhagena","sequence":"additional","affiliation":[{"name":"Laboratory of Catalysis and Organic Synthesis Institute of Chemical Sciences and Engineering, \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne  Lausanne CH\u20101015 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4570-914X","authenticated-orcid":false,"given":"Jerome","family":"Waser","sequence":"additional","affiliation":[{"name":"Laboratory of Catalysis and Organic Synthesis Institute of Chemical Sciences and Engineering, \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne  Lausanne CH\u20101015 Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,6,8]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm300094u"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1MD00043H"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201700082"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02812E"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0043-1775395"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.6b00281"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.7b00018"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2023.115412"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23071499"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202100277"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-06202-4"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/40.3.441"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.0c00851"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00885a021"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar700098d"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100031f"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1378706"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.20074"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.3390\/catal10111339"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2022.114255"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lfs.2024.122904"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610314"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201900589"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.3c00014"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3QO01631E"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC05100A"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205103"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4GC05166A"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200004)2000:7<1137::AID-EJOC1137>3.0.CO;2-2"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201909655"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c03913"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b11218"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202310462"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201914875"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201603955"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.202000191"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC05573D"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC02249K"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201701296"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c02267"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201202977"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC04525K"},{"key":"e_1_2_6_43_1","unstructured":"Deposition numbers2443049 (for EBX.2) and 2443048 (for 29a) contain the supplementary crystallographic data for this paper.These data are provided free of chargefrom the Cambridge Crystallographic Data Centre."},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.202200126"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03990"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c04140"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202000653"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b00659"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202306128"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202006707"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c02869"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201903392"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC04738A"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c02201"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b11099"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202508404","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,2]],"date-time":"2025-12-02T09:25:09Z","timestamp":1764667509000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202508404"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,6,8]]},"references-count":55,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2025,8,4]]}},"alternative-id":["10.1002\/anie.202508404"],"URL":"https:\/\/doi.org\/10.1002\/anie.202508404","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,6,8]]},"assertion":[{"value":"2025-04-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-28","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-06-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202508404"}}