Long-wavelength Fluorogenic Derivatization of Aryl Halides Based on the Formation of Stilbene by Heck Reaction with Vinylbenzenes

• HIGASHIJIMA Takumi

  Graduate School of Biomedical Sciences, Course of Pharmaceutical Sciences, Nagasaki University

• KISHIKAWA Naoya

  Graduate School of Biomedical Sciences, Course of Pharmaceutical Sciences, Nagasaki University

• KURODA Naotaka

  Graduate School of Biomedical Sciences, Course of Pharmaceutical Sciences, Nagasaki University

抄録

The long-wavelength fluorogenic derivatization method for aryl halides was developed based on stilbene formation by the Heck coupling reaction between aryl halides and vinylbenzenes in the presence of palladium(II) acetate as a catalyst. Fluorescent maximum wavelengths of the derivative obtained by the proposed reaction were 365 – 450 nm, which were 50 – 100 nm longer than those of the biphenyl derivatives formed with our previously developed fluorogenic derivatization method. Also, by the investigation using vinylbenzenes containing electron-donating or -withdrawing functional groups, it was found that an internal charge transfer system could contribute to extend the emission wavelength of the derivative. Furthermore, the proposed reaction was applied to develop a pre-column derivatization HPLC with fluorescence detection method for aryl bromides using 4-vinylanisole. p-Substituted aryl bromide derivatives (i.e., p-bromobenzonitrile, p-bromoanisole, bromobenzene, p-bromobenzoic acid ethyl ester, p-bromotoluene) were successfully detected within 40 min with the detection limit of 0.007 – 0.264 μM. Despite the short reaction time of 10 min, the reaction yields for p-bromoanisole and bromobenzene were good at 101 and 87%, respectively.

収録刊行物

• Analytical Sciences

  Analytical Sciences 36 (8), 997-1001, 2020-08-10

  社団法人 日本分析化学会

キーワード

• Fluorogenic derivatization
• Heck reaction

詳細情報

• CRID: 1390003825205096320
• NII論文ID: 130007886464
• NII書誌ID: AA10500785
• DOI: 10.2116/analsci.20p031
• ISSN: 13482246
• ISSN: 09106340
• HANDLE: 10069/40223
• NDL書誌ID: 030563810
• PubMed: 32173676
• Web Site: https://nagasaki-u.repo.nii.ac.jp/records/1024
• Web Site: http://id.ndl.go.jp/bib/030563810
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030563810
• Web Site: https://link.springer.com/content/pdf/10.2116/analsci.20P031.pdf
• Web Site: https://link.springer.com/article/10.2116/analsci.20P031/fulltext.html
• Web Site: https://www.jstage.jst.go.jp/article/analsci/36/8/36_20P031/_pdf
• 本文言語コード: en
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