{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T00:20:54Z","timestamp":1760660454935,"version":"build-2065373602"},"reference-count":19,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2023,11,13]],"date-time":"2023-11-13T00:00:00Z","timestamp":1699833600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["21K07687","23H02867"],"award-info":[{"award-number":["21K07687","23H02867"]}],"id":[{"id":"10.13039\/501100001691","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":[[2024,5,30]]},"abstract":"<jats:p>A labeling technique was developed for the imidazoline I<jats:sub>2<\/jats:sub> receptor ligand 2\u2010(3\u2010fluoro\u2010tolyl)\u20104, 5\u2010dihydro\u20101H\u2010imidazole (FTIMD) using Pd(0)\u2010mediated <jats:sup>11<\/jats:sup>C\u2010carbomethoxylation with [<jats:sup>11<\/jats:sup>C]CO, followed by imidazoline ring formation with ethylenediamine\u2010trimethylaluminium (EDA\u2010AlMe<jats:sub>3<\/jats:sub>). To achieve this, [<jats:sup>11<\/jats:sup>C]CO was passed through a methanol (MeOH) solution containing 3\u2010fluoro\u20104\u2010methylphenylboronic acid (<jats:bold>1<\/jats:bold>), palladium (II) acetate (Pd [OAc]<jats:sub>2<\/jats:sub>), triphenylphosphine (PPh<jats:sub>3<\/jats:sub>), and <jats:italic>p<\/jats:italic>\u2010benzoquinone (PBQ). The mixture was then heated at 65\u00b0C for 5\u00a0min. EDA was introduced into the reaction mixture, and MeOH was completely evaporated at temperatures exceeding 100\u00b0C. The dried reaction mixture was combined with an EDA\u2010AlMe (1:1) toluene solution and heated at 145\u00b0C for 10\u00a0min. Portions of the reaction mixture were analyzed through high\u2010performance liquid chromatography, resulting in [<jats:sup>11<\/jats:sup>C]FTIMD with 26% (<jats:italic>n<\/jats:italic>\u00a0=\u20092) decay\u2010corrected radiochemical yield (RCY). This method could be utilized for various arylborons to produce [2\u2010<jats:sup>11<\/jats:sup>C]imidazolines <jats:bold>4a<\/jats:bold>\u2013<jats:bold>h<\/jats:bold> with RCYs ranging from low to moderate. Notably, [2\u2010<jats:sup>11<\/jats:sup>C]benazoline was obtained with a moderate RCY of 65%. The proposed technique serves as an alternative to the Grignard method, which uses [<jats:sup>11<\/jats:sup>C]CO to generate a [2\u2010<jats:sup>11<\/jats:sup>C]\u2010labeled imidazoline ring.<\/jats:p>","DOI":"10.1002\/jlcr.4072","type":"journal-article","created":{"date-parts":[[2023,11,13]],"date-time":"2023-11-13T21:35:29Z","timestamp":1699911329000},"page":"227-234","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Novel synthesis of <sup>11<\/sup>C\u2010labeled imidazolines via Pd(0)\u2010mediated <sup>11<\/sup>C\u2010carbomethoxylation using [<sup>11<\/sup>C]CO and arylborons"],"prefix":"10.1002","volume":"67","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2408-4897","authenticated-orcid":false,"given":"Hideki","family":"Ishii","sequence":"first","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Katsuyuki","family":"Minegishi","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kotaro","family":"Nagatsu","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nobuki","family":"Nengaki","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"},{"name":"SHI Accelerator Service Ltd.  Tokyo Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ming\u2010Rong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,11,13]]},"reference":[{"issue":"1","key":"e_1_2_7_2_1","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1016\/S0022-3565(25)21405-7","article-title":"Central cardiovascular effects of alpha adrenergic drugs: differences between catecholamines and imidazolines","volume":"230","author":"Bousquet P","year":"1984","journal-title":"J Pharmacol Exp Ther"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0895\u20107061(00)00223\u20105"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1089\/10445490050043290"},{"key":"e_1_2_7_5_1","first-page":"757","article-title":"Imidazoline receptors: basic knowledge, recent advances and future prospects for therapy","volume":"22","author":"Molderings GJ","year":"1997","journal-title":"Drug Future"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/jcbfm.1992.7"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1179\/174313209X444116"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejphar.2009.11.063"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.746"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nucmedbio.2011.07.008"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nucmedbio.2014.12.014"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.2967\/jnumed.112.108258"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nucmedbio.2010.02.013"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nucmedbio.2011.06.001"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.01.008"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01166a028"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200505405"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/om00037a025"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462569"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00326a055"}],"container-title":["Journal of Labelled Compounds and Radiopharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jlcr.4072","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T13:50:06Z","timestamp":1760622606000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jlcr.4072"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,11,13]]},"references-count":19,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2024,5,30]]}},"alternative-id":["10.1002\/jlcr.4072"],"URL":"https:\/\/doi.org\/10.1002\/jlcr.4072","archive":["Portico"],"relation":{},"ISSN":["0362-4803","1099-1344"],"issn-type":[{"type":"print","value":"0362-4803"},{"type":"electronic","value":"1099-1344"}],"subject":[],"published":{"date-parts":[[2023,11,13]]},"assertion":[{"value":"2023-06-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-10-16","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-11-13","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}