A New Pathway for Synthesis of Ketone from Aldehyde and Sulfonylhydrazone: Is Diazo the Key Intermediate?

A new pathway via a cyclic intermediate for synthesis of ketone from aldehyde and sulfonylhydrazone derivative under base condition was proposed by performing several control experiments along with analyzing the mass spectra and in situ IR of the reaction mixture. Inspired by the new mechanism, an e...

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Published inChemistry : a European journal p. e202301569
Main Authors Wang, Yue-Xing, Chen, Li-Ping, Cao, Feng-de, Zhao, Bin, Li, Zhen-Peng, Li, Xiu-Fen, Huang, Longjiang
Format Journal Article
LanguageEnglish
Published Germany 02.07.2023
Subjects
3-(Trifluoromethyl) benzenesulfonylhydrazone Aldehyde Base Ketone Synthesis
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Summary:A new pathway via a cyclic intermediate for synthesis of ketone from aldehyde and sulfonylhydrazone derivative under base condition was proposed by performing several control experiments along with analyzing the mass spectra and in situ IR of the reaction mixture. Inspired by the new mechanism, an efficient and scalable method for homologation of aldehydes to ketones has been developed. The wide variety of target ketones were obtained in yields of 42-95% by simply heating the 3-(Trifluoromethyl)benzene sulfonylhydrazones (3-(Tfsyl)hydrazone) with aldehydes at 110 °C in 2 hours with K2CO3 and DMSO as base and solvent, respectively.
ISSN:1521-3765