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The Utility of Sonogashira Coupling Reaction for the Derivatization of Aryl Halides with Fluorescent Alkyne
http://hdl.handle.net/10069/38689
http://hdl.handle.net/10069/3868955b8133e-2bac-4b88-934d-f377359c8878
名前 / ファイル | ライセンス | アクション |
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AnaSci34_1183.pdf (486.3 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2018-11-13 | |||||
タイトル | ||||||
タイトル | The Utility of Sonogashira Coupling Reaction for the Derivatization of Aryl Halides with Fluorescent Alkyne | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Fluorescence derivatization | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Fluorescent alkyne | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Ortho-substituted aryl halide | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Sonogashira coupling reaction | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
YASAKA, Naoyuki
× YASAKA, Naoyuki× KISHIKAWA, Naoya× HIGASHIJIMA, Takumi× OHYAMA, Kaname× KURODA, Naotaka |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | Aryl halides are a very important category of compounds that include many vital drugs and key industrial additives, such as clofibrate and bromobenzene, respectively. Due to their importance, our research group previously developed a novel fluorescence labeling approach for their analysis using a fluorescent aryl boronic acid as a reagent, based on the Suzuki coupling reaction. This coupling reaction was successfully applied for the determination of aryl halides in biological fluids; however, there was a limitation of low reactivity towards ortho-substituted aryl halides. In the present study, a novel fluorescence derivatization approach for aryl halides was developed using, 2-(4-ethynylphenyl)-4,5-diphenyl-1Himidazole (DIB-ET) as a fluorescent alkyne reagent, based on the Sonogashira coupling reaction. DIB-ET reacted with aryl bromides in the presence of palladium and copper as catalysts, yielding fluorescent derivatives that could be subsequently determined by an HPLC system with fluorescence detection. The detection limits (S/N = 3) for aryl bromides were in the range of 14 - 23 nM, which is 3.5 - 18-times more sensitive than our previously developed approach, Suzuki coupling derivatization. Moreover, in contrast to the previous technique, the reactivity of DIB-ET to orthosubstituted aryl bromides was almost equivalent to that of the para-substituted aryl bromides. Hence, by using this newly developed approach we could label the aryl halides with more sensitivity and reactivity. Finally, the proposed method was successfully applied for the selective determination of aryl bromides in human serum with good recovery (84.6 - 107%), which proves the ability of the developed method to determine occupational exposure to aryl halides. | |||||
書誌情報 |
Analytical Sciences 巻 34, 号 10, p. 1183-1188, 発行日 2018-10-10 |
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出版者 | ||||||
出版者 | 日本分析化学会 | |||||
出版者別言語 | ||||||
Japan Society for Analytical Chemistry | ||||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 09106340 | |||||
EISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 13482246 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.2116/analsci.18P117 | |||||
権利 | ||||||
権利情報 | 2018 cThe Japan Society for Analytical Chemstry | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Analytical sciences, 34(10), pp.1183-1188; 2018 |