One-Step Synthesis of Arylacetaldehydes from Aryl Aldehydes or Diaryl Ketones via One-Carbon Extension by Using the System of DMSO/KOH/Zinc,Advanced Synthesis & Catalysis

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One-Step Synthesis of Arylacetaldehydes from Aryl Aldehydes or Diaryl Ketones via One-Carbon Extension by Using the System of DMSO/KOH/Zinc
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-07-18 , DOI: 10.1002/adsc.202200437
Zhiwen Nie ₁ , Tonglin Yang ₂ , Miaodong Su ₂ , Wei-Ping Luo ₂ , qiang Liu ₁ , Can-Cheng Guo ₁

Affiliation

A one-step protocol is described for the synthesis of arylacetaldehydes from aryl aldehydes or diaryl ketones by using the system of DMSO/KOH/zinc. In this transformation, DMSO provides a methine fragment that converts the −CHO structure in aryl aldehydes or the −CO− structure in diaryl ketones to the −CH₂CHO structure in arylacetaldehydes via a one-carbon extension. This protocol could also be used to synthesize arylacetaldehyde acetals from aryl aldehydes or diaryl ketones when zinc was replaced by diols. In this protocol, 25 examples of arylacetaldehydes and 26 examples of arylacetaldehyde acetals have been synthesized from aryl aldehydes or diaryl ketones. Based on control experiments and the literature, a plausible reaction mechanism is proposed in our work.

中文翻译：

DMSO/KOH/Zinc体系一碳扩链一步合成芳基乙醛或二芳基酮

描述了使用 DMSO/KOH/锌系统从芳基醛或二芳基酮合成芳基乙醛的一步法。在这种转化中，DMSO 提供了一个次甲基片段，该片段通过单碳延伸将芳基醛中的 -CHO 结构或二芳基酮中的 -CO- 结构转化为芳基乙醛中的 -CH ₂ CHO 结构。当锌被二醇取代时，该协议还可用于从芳基醛或二芳基酮合成芳基乙醛缩醛。在该协议中，芳基醛或二芳基酮合成了 25 个芳基乙醛和 26 个芳基乙醛缩醛的例子。基于对照实验和文献，我们的工作提出了一种合理的反应机制。

更新日期：2022-07-18

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