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 in | Chemistry : a European journal p. e202301569 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
02.07.2023
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| Subjects | |
| Online Access | Get full text |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Li, Zhen-Peng Li, Xiu-Fen Cao, Feng-de Huang, Longjiang Zhao, Bin Chen, Li-Ping Wang, Yue-Xing |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37394679$$D View this record in MEDLINE/PubMed |
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| Keywords | 3-(Trifluoromethyl) benzenesulfonylhydrazone Aldehyde Base Ketone Synthesis |
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| Snippet | A new pathway via a cyclic intermediate for synthesis of ketone from aldehyde and sulfonylhydrazone derivative under base condition was proposed by performing... |
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| Title | A New Pathway for Synthesis of Ketone from Aldehyde and Sulfonylhydrazone: Is Diazo the Key Intermediate? |
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