{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,1]],"date-time":"2026-05-01T21:02:53Z","timestamp":1777669373225,"version":"3.51.4"},"reference-count":26,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2022,12,27]],"date-time":"2022-12-27T00:00:00Z","timestamp":1672099200000},"content-version":"am","delay-in-days":358,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2022,1,3]],"date-time":"2022-01-03T00:00:00Z","timestamp":1641168000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003554","name":"Lundbeckfonden","doi-asserted-by":"publisher","award":["R277\u20102018\u2010260"],"award-info":[{"award-number":["R277\u20102018\u2010260"]}],"id":[{"id":"10.13039\/501100003554","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE\u20101951518"],"award-info":[{"award-number":["CHE\u20101951518"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004240","name":"Akademie V\u011bd \u010cesk\u00e9 Republiky","doi-asserted-by":"publisher","award":["RVO 61388963"],"award-info":[{"award-number":["RVO 61388963"]}],"id":[{"id":"10.13039\/501100004240","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Labelled Comp Radiopharmac"],"published-print":{"date-parts":[[2022,2]]},"abstract":"<jats:p>The multifunctional radioligand [<jats:sup>3<\/jats:sup>H]T0901317 ([<jats:sup>3<\/jats:sup>H]<jats:bold>1<\/jats:bold>) has been employed as a powerful autoradiographic tool to target several receptors, such as liver X, farnesoid X, and retinoic acid\u2010related orphan receptor alpha and gamma subtypes at nanomolar concentrations. Although [<jats:sup>3<\/jats:sup>H]<jats:bold>1<\/jats:bold> is commercially available and its synthesis via tritiodebromination has been reported, the market price of this radioligand and the laborious synthesis of corresponding bromo\u2010intermediate potentially preclude its widespread use in biochemical, pharmacological, and pathological studies in research lab settings. We exploit recent reports on hydrogen\u2010isotope exchange (HIE) reactions in tertiary benzenesulfonamides where the sulfonamide represents an <jats:italic>ortho<\/jats:italic>\u2010directing group that facilitates C\uf8ffH activation in the presence of homogenous iridium(I) catalysts. Herein, we report a time\u2010 and cost\u2010efficient method for the tritium late\u2010stage labeling of compound <jats:bold>1<\/jats:bold>\u2014a remarkably electron\u2010poor substrate owing to the tertiary trifluoroethylsulfonamide moiety. Under a straightforward HIE condition using a commercially available Kerr\u2010type NHC Ir(I) complex, [(cod)Ir (NHC)Cl], the reaction with <jats:bold>1<\/jats:bold> afforded a specific activity of 10.8\u00a0Ci\/mmol. Additionally, alternative HIE conditions using the heterogeneous catalyst of Ir\u2010black provided sufficient 0.72 D\u2010enrichment of <jats:bold>1<\/jats:bold> but unexpectedly failed while repeating with tritium gas.<\/jats:p>","DOI":"10.1002\/jlcr.3958","type":"journal-article","created":{"date-parts":[[2021,12,27]],"date-time":"2021-12-27T04:43:59Z","timestamp":1640580239000},"page":"36-44","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Tritium hydrogen\u2010isotope exchange with electron\u2010poor tertiary benzenesulfonamide moiety; application in late\u2010stage labeling of T0901317"],"prefix":"10.1002","volume":"65","author":[{"given":"Tian","family":"Yongsong","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry The Czech Academy of Sciences  Prague Czech Republic"},{"name":"Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences University of Copenhagen  Copenhagen Denmark"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"B\u0159etislav","family":"Bro\u017e","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry The Czech Academy of Sciences  Prague Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Franti\u0161ek","family":"Ture\u010dek","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Washington  Seattle Washington USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9031-8263","authenticated-orcid":false,"given":"Ale\u0161","family":"Marek","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry The Czech Academy of Sciences  Prague Czech 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