Presentation Pd(0)-mediated [11C]carbonylation of boronic acid pinacol esters with [11C]carbon monoxide and the facile conversion of [carbonyl-11C]esters to [carbonyl-11C]amides

Ishii, Hideki  ,  Minegishi, Katsuyuki  ,  Nagatsu, Koutarou  ,  Ming-Rong, Zhang

Objectives: Introduction of carbonyl moiety into an aryl or heteroaryl group are powerful processes for the construction of valuable pharmacophore. However typical carbonylation reaction using [11C]O generally requires high pressure and high temperature conditions. Therefore, the development of convenient method for the [11C]carbonylation reaction is needed. Here we present the Pd(0)-mediated mild [11C]carbonylation reaction using [11C]O and boronic acid pinacol esters. Methods: The [11C]O, which prepared from [11C]O2, was reacted with aryl and heteroarylboronic acid pinacol esters in the presence of p-benzoquinone and triphenylphosphine in MeOH or DMF-MeOH (v/v =1:1) at 65 °C under atmospheric pressure for 5 min to give corresponding [11C]esters. Some of these [11C]esters were converted to corresponding [11C]amides by treatment with 25% ammonia solution 65 °C for 5 min. Scheme 1. Radiosynthesis of [carbonyl-11C]esters and [carbonyl-11C]amidesResults: Various aryl/heteroaryl boronates were converted to the corresponding [carbonyl-11C]esters with decay-corrected radiochemical yield in the range of 6-80% Conclusions: Acknowledgeme
21st International Symposium on Radiopharmaceutical Sciences

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