{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T15:10:02Z","timestamp":1789744202030,"version":"4.0.1"},"reference-count":51,"publisher":"American Chemical Society (ACS)","issue":"37","license":[{"start":{"date-parts":[[2026,9,6]],"date-time":"2026-09-06T00:00:00Z","timestamp":1788652800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","award":["1.1.1.5\/2\/24\/A\/001"],"award-info":[{"award-number":["1.1.1.5\/2\/24\/A\/001"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,18]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Fluorinated bicyclo[1.1.1]pentanes (F-BCPs) are valuable three-dimensional bioisosteres in drug discovery, yet methods for the direct construction of bridge-monofluorinated and quaternary F-BCPs remain scarce. Here, we report a fluoroiodocarbene addition to bicyclobutanes under mild conditions, providing 2-fluoro-2-iodobicyclo[1.1.1]pentanes. The C\u2013I bond serves as a versatile radical handle, enabling synthesis of quaternary bridge-fluorinated BCPs, including Giese-type additions to activated alkenes and desulfonylative couplings. This strategy offers a practical, modular entry to bridge-fluorinated BCP architectures of potential interest for medicinal chemistry.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03112","type":"journal-article","created":{"date-parts":[[2026,9,6]],"date-time":"2026-09-06T16:01:27Z","timestamp":1788710487000},"page":"11523-11528","source":"Crossref","is-referenced-by-count":0,"title":["Fluoroiodocarbene Addition to Bicyclobutanes: A Radical\nHandle for Quaternary Fluorinated Bicyclo[1.1.1]pentanes"],"prefix":"10.1021","volume":"28","author":[{"given":"Arturs","family":"Sperga","sequence":"first","affiliation":[{"name":"National Institute of Research and Innovation , Aizkraukles Street 21 , ,","place":["Riga, Latvia, LV-1006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Toms","family":"Pfeifers","sequence":"additional","affiliation":[{"name":"National Institute of Research and Innovation , Aizkraukles Street 21 , ,","place":["Riga, Latvia, LV-1006"]},{"name":"University of Latvia , , Jelgavas Street 1 , ,","place":["Riga, Latvia, LV-1004"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Artis","family":"Kinens","sequence":"additional","affiliation":[{"name":"National Institute of Research and Innovation , Aizkraukles Street 21 , ,","place":["Riga, Latvia, LV-1006"]},{"name":"University of Latvia , , Jelgavas Street 1 , ,","place":["Riga, Latvia, LV-1004"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0955-8257","authenticated-orcid":true,"given":"Janis","family":"Veliks","sequence":"additional","affiliation":[{"name":"National Institute of Research and Innovation , Aizkraukles Street 21 , ,","place":["Riga, Latvia, LV-1006"]},{"name":"Riga Technical University , , Paula Valdena Street 3 , ,","place":["Riga, Latvia, LV-1048"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,6]]},"reference":[{"issue":"21","key":"2026091809413673000_cit1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.202200365","article-title":"Fluorinated Cycloalkyl\nBuilding Blocks for Drug Discovery","volume":"17","author":"Grygorenko","year":"2022","journal-title":"ChemMedChem"},{"issue":"6","key":"2026091809413673000_cit2","doi-asserted-by":"publisher","first-page":"1539","DOI":"10.1021\/jacsau.3c00014","article-title":"Conquering the Synthesis and Functionalization of Bicyclo[1.1.1]pentanes","volume":"3","author":"Shire","year":"2023","journal-title":"JACS Au"},{"issue":"47","key":"2026091809413673000_cit3","doi-asserted-by":"publisher","first-page":"24754","DOI":"10.1002\/anie.202106352","article-title":"Bridge Functionalisation\nof Bicyclo[1.1.1]pentane Derivatives","volume":"60","author":"Anderson","year":"2021","journal-title":"Angew.\nChem., Int. 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WO Patent 2019141179, 2019."},{"key":"2026091809413673000_cit8","unstructured":"Chen, J. L.; Chen, Y.-H.; Dimauro, E. F.; Lu, M.; Methot, J. L.; Musacchio, A. J.; Palani, A.; Pio, B.; Rico Duque, L.; Siliphaivanh, P.; Vara, B. A.\n          Triazolinone compound\nas RIPK1 inhibitor. WO Patent 2023225041, 2023."},{"issue":"29","key":"2026091809413673000_cit9","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205103","article-title":"A Practical\nand Scalable Approach to Fluoro-Substituted\nBicyclo[1.1.1]pentanes","volume":"61","author":"Bychek","year":"2022","journal-title":"Angew. Chem., Int. Ed."},{"issue":"44","key":"2026091809413673000_cit10","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2524130122","article-title":"Dibromocarbene addition to bicyclo[1.1.0]butanes:\nA facile route to substituted bicyclo[1.1.1]pentanes","volume":"122","author":"Attard","year":"2025","journal-title":"Proc. Natl. Acad. Sci. U. S. 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Am. Chem. Soc."},{"issue":"2","key":"2026091809413673000_cit33","doi-asserted-by":"publisher","first-page":"2292","DOI":"10.1021\/acs.chemrev.1c00558","article-title":"Applications of Halogen-Atom Transfer\n(XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry\nand Photocatalysis","volume":"122","author":"Julia\u0301","year":"2022","journal-title":"Chem. Rev."},{"key":"2026091809413673000_cit34","doi-asserted-by":"publisher","first-page":"28034","DOI":"10.1021\/jacs.4c06774","article-title":"Radical Polarity","volume":"146","author":"Garwood","year":"2024","journal-title":"J. Am. Chem. 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B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.\n          Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2013."},{"key":"2026091809413673000_cit48","doi-asserted-by":"publisher","first-page":"1057","DOI":"10.1039\/b515623h","article-title":"Accurate Coulomb-fitting\nbasis sets for H to Rn","volume":"8","author":"Weigend","year":"2006","journal-title":"Physical Chemistry Chemical\nPhysics"},{"key":"2026091809413673000_cit49","doi-asserted-by":"publisher","first-page":"34427","DOI":"10.1021\/jacs.4c10968","article-title":"Catalytic\nIntermolecular Asymmetric [2\u03c0 + 2\u03c3] Cycloadditions of\nBicyclo[1.1.0]butanes: Practical Synthesis of Enantioenriched Highly\nSubstituted Bicyclo[2.1.1]hexanes","volume":"146","author":"Li","year":"2024","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026091809413673000_cit50","doi-asserted-by":"publisher","first-page":"27204","DOI":"10.1021\/jacs.4c11296","article-title":"Formal [2\u03c3\n+ 2\u03c3]-Cycloaddition of Aziridines with Bicyclo[1.1.0]butanes:\nAccess to Enantiopure 2-Azabicyclo[3.1.1]heptane Derivatives","volume":"146","author":"Dutta","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026091809413673000_cit51","doi-asserted-by":"publisher","first-page":"27204","DOI":"10.1021\/jacs.4c11296","article-title":"Formal [2\u03c3\n+ 2\u03c3]-Cycloaddition of Aziridines with Bicyclo[1.1.0]butanes:\nAccess to Enantiopure 2-Azabicyclo[3.1.1]heptane Derivatives","volume":"146","author":"Dutta","year":"2024","journal-title":"J. Am. Chem. Soc."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c03112","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/37\/11523\/68396618\/acs.orglett.6c03112.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/37\/11523\/68396618\/acs.orglett.6c03112.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T14:57:18Z","timestamp":1789743438000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/37\/11523\/5421935\/Fluoroiodocarbene-Addition-to-Bicyclobutanes-A"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,6]]},"references-count":51,"journal-issue":{"issue":"37","published-online":{"date-parts":[[2026,9,6]]},"published-print":{"date-parts":[[2026,9,18]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c03112","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,6]]}}}