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

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Title: Long-wavelength Fluorogenic Derivatization of Aryl Halides Based on the Formation of Stilbene by Heck Reaction with Vinylbenzenes
Authors: HIGASHIJIMA, Takumi / KISHIKAWA, Naoya / KURODA, Naotaka
Issue Date: 10-Aug-2020
Publisher: 日本分析化学会 / The Japan Society for Analytical Chemistry
Citation: Analytical sciences, 36(8), pp.997-1001; 2020
Abstract: 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.
Keywords: Fluorogenic derivatization / Heck reaction
URI: http://hdl.handle.net/10069/40223
ISSN: 09106340
DOI: 10.2116/analsci.20P031
Rights: © 2020 by The Japan Society for Analytical Chemistry
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/40223

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