Synthesis of 11C-/13C-Ketones by Suzuki Coupling
2004 (English)In: Eur. J. Org. Chem., 474-478 p.Article in journal (Refereed) Published
Aryl triflates, methyl- or arylboronic acids, and a low concentration of [11C]carbon monoxide were employed on small scale in the syntheses of fifteen 11C-labelled ketones using palladium-mediated Suzuki coupling reactions. The reagents were confined in a micro-autoclave and heated at 150C for 5 min. The reaction required the presence of LiBr, but no additional base. The 11C-labelled products were obtained with decay-corrected radiochemical yields in the range 10-70% and with high specific radioactivity (150-640 GBq/umol). The radiochemical purity of the final products exceeded 98%. One 13C-substituted ketone ([13C]-2'-benzonaphthone)was prepared and analysed by NMR spectroscopy for confirmation of the labelling position. The reference compound 2'-benzonaphthone was prepared by a palldium-catalysed reaction between sodium tetraphenylborate and 2-naphthoyl chloride. 2-Thienyl p-tolyl ketone, 4-nitrophenyl 2-thienyl ketone an d2-naphthyl 2-thienyl ketone were prepared by reactions between thiophene-2-boronic acid and the corresponding acid chlorides. The presented approach is novel and seems to be an efficient method for the synthesis of a wide range of 11C- as well as 13C-labelled ketones.
Place, publisher, year, edition, pages
2004. 474-478 p.
Aryl triflates, Boronic acids, Isotope labelling, Ketones
IdentifiersURN: urn:nbn:se:uu:diva-69931DOI: doi:10.1002/ejoc.200300527OAI: oai:DiVA.org:uu-69931DiVA: diva2:97842