Aza-Wittig reaction of (β-diazo-α,α-difluoroethyl)phosphonates with aldehydes for the synthesis of difluoromethylphosphonate-containing arylidene hydrazones

IF 1.7 4区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Fluorine Chemistry Pub Date : 2023-11-29 DOI:10.1016/j.jfluchem.2023.110226
Qian Wang , Romana Pajkert , Haibo Mei , Gerd-Volker Röschenthaler , Jianlin Han
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Abstract

An aza-Wittig reaction of in situ generated difluoroalkyl diazo analog, (β-diazo-α,α-difluoroethyl)phosphonates, with aldehyde under mild conditions has been developed to afford difluoromethylphosphonate-containing arylidene hydrazones up to 99 % yields. The reaction was carried out under mild conditions with a broad substrate scope and was suitable for scale-up application. This reaction provides an efficient method for the facile construction of a series of difluoromethylphosphonate-containing arylidene hydrazones and is also a useful supplement to the transformation of (β-diazo-α,α-difluoroethyl)phosphonates.

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(β-重氮-α,α-二氟乙基)膦酸盐与醛的Aza-Wittig反应合成含二氟甲基膦酸芳基腙
以原位合成的二氟烷基重氮类似物(β-重氮-α,α-二氟乙基)膦酸盐与醛在温和条件下进行aza-Wittig反应,产率可达99%。该反应在温和的条件下进行,底物范围广,适合扩大应用。该反应为一系列含二氟甲基膦酸甲酰芳基腙的便捷构建提供了一种有效的方法,也是(β-重氮-α,α-二氟乙基)膦酸盐转化的有益补充。
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来源期刊
Journal of Fluorine Chemistry
Journal of Fluorine Chemistry 化学-无机化学与核化学
CiteScore
3.80
自引率
10.50%
发文量
99
审稿时长
33 days
期刊介绍: The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature. For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.
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