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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Bibliographic Details
Published in:Chemistry : a European journal 2023-07, p.e202301569
Main Authors: Wang, Yue-Xing, Chen, Li-Ping, Cao, Feng-de, Zhao, Bin, Li, Zhen-Peng, Li, Xiu-Fen, Huang, Longjiang
Format: Article
Language:English
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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
DOI:10.1002/chem.202301569