Nucleophilic Addition to Nitrones Using a Flow Microreactor,Synlett

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Nucleophilic Addition to Nitrones Using a Flow Microreactor
Synlett ( IF 1.7 ) Pub Date : 2020-02-18 , DOI: 10.1055/s-0039-1691601
Yasushi Imada ₁ , Yukihiro Arakawa ₁ , Shun Ueta ₁ , Takuma Okamoto ₁ , Keiji Minagawa _{1,

2}

Affiliation

Nucleophilic addition reactions of soft carbon nucleophiles to nitrones in a flow microreactor are reported for the first time. Under microflow conditions at 30 to 0 °C, a range of nitrones can be efficiently transformed into the corresponding oxyiminium ions by reaction with either acyl halides or trialkylsilyl triflates. These can subsequently undergo the addition of nucleophiles including allyltributylstannane, ketene methyl tert-butyldimethylsilyl acetal, and N-silyl ketene imines to afford the corresponding adducts in high yields; such reactions at a similar temperature under batch conditions resulted in lower yields because of undesired side reactions.

中文翻译：

使用流动微反应器对硝酮进行亲核加成

首次报道了在流动微反应器中软碳亲核试剂与硝酮的亲核加成反应。在 30 至 0 °C 的微流条件下，通过与酰卤或三烷基甲硅烷基三氟甲磺酸酯反应，可以将一系列硝酮有效地转化为相应的氧亚胺离子。这些随后可以添加亲核试剂，包括烯丙基三丁基锡烷、烯酮甲基叔丁基二甲基甲硅烷基乙缩醛和 N-甲硅烷基烯酮亚胺，以高产率提供相应的加合物；由于不希望有的副反应，在类似温度下在分批条件下的此类反应导致较低的产率。

更新日期：2020-02-18

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