A New Pathway for the Synthesis of Ketones from Aldehydes and Sulfonylhydrazones: Is Diazo the Key Intermediate?

IF 3.9 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - A European Journal Pub Date : 2023-07-02 DOI:10.1002/chem.202301569

Yue-xing Wang, Li-ping Chen, Feng-de Cao, Bin Zhao, Zhen-peng Li, Xiu-fen Li, Dr. Long-jiang Huang

引用次数: 0

Abstract

A new pathway via a cyclic intermediate for the synthesis of ketones from aldehydes and sulfonylhydrazone derivatives under basic conditions is proposed. Several control experiments were performed along with analysis of the mass spectra and in-situ IR spectra of the reaction mixture. Inspired by the new mechanism, an efficient and scalable method for homologation of aldehydes to ketones was developed. A wide variety of target ketones were obtained in yields of 42–95 % by simply heating the 3-(trifluoromethyl)benzene sulfonylhydrazones (3-(Tfsyl)hydrazone) for 2 h at 110 °C with aldehydes and with K₂CO₃ and DMSO as base and solvent, respectively.

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醛和磺酰腙合成酮的新途径：二偶氮是关键中间体吗？

提出了在碱性条件下由醛和磺酰腙衍生物通过环状中间体合成酮的新途径。进行了几个对照实验，同时分析了反应混合物的质谱和原位红外光谱。受这一新机理的启发，开发了一种高效、可扩展的醛与酮的同源方法。以42–95的产率获得了多种目标酮 % 通过简单地将3-（三氟甲基）苯磺酰腙（3-（Tfsyl）腙）加热2 110时的h °C，分别用醛和K2CO3和DMSO作为碱和溶剂。

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来源期刊

Chemistry - A European Journal 化学-化学综合

CiteScore

7.90

自引率

4.70%

发文量

1808

审稿时长

1.8 months

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