@article{oai:repo.qst.go.jp:00046744,
 author = {Kikuchi, Tatsuya and Minegishi, Katsuyuki and Hashimoto, Hiroki and Zhang, Ming-Rong and Kato, Koichi and 菊池 達矢 and 峯岸 克行 and 橋本 裕輝 and 張 明栄 and 加藤 孝一},
 issue = {13},
 journal = {Journal of Labelled Compounds & Radiopharmaceuticals},
 month = {Jul},
 note = {The N- or O-methylation reactions of compounds bearing amide, aniline, or phenol moieties using iodo[11C]methane (1) with
the aid of a base are frequently applied to the preparation of 11C-labeled radiopharmaceuticals. Although sodium hydride
and alkaline metal hydroxides are commonly employed as bases in these reactions, their poor solubility properties in
organic solvents and hydrolytic activities have sometimes limited their application and made the associated 11C-methylation
reactions difficult. In contrast to these bases, tetrabutylammonium fluoride (TBAF) is moderately basic, highly soluble in
organic solvents, and weakly nucleophilic. Although it was envisaged that TBAF could be used as the preferred base for
11C-methylation reactions using 1, studies concerning the use of TBAF to promote 11C-methylation reactions are scarce.
Herein, we have evaluated the efficiency of the 11C-methylation reactions of 13 model compounds using TBAF and 1. In most
cases, the N-11C-methylations were efficiently promoted by TBAF in dimethyl sulfoxide at ambient temperature, whereas the
O-11C-methylations required heating in some cases. Comparison studies revealed that the efficiencies of the 11C-methylation
reactions with TBAF were comparable or sometimes greater than those conducted with sodium hydride. Based on these
results, TBAF should be considered as the preferred base for 11C-methylation reactions using 1.},
 pages = {672--678},
 title = {The use of tetrabutylammonium fluoride to promote N- and O-11C-methylation reactions with iodo[11C]methane in dimethyl sulfoxide},
 volume = {56},
 year = {2013}
}