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Abstract
α-Keto aldehydes are flexible and versatile synthetic building blocks widely used for
constructing heterocyclic systems. However, classical methods for synthesizing α-keto aldehydes, based
on the oxidation of the corresponding methyl ketones, cannot be employed for the synthesis of α-
monosubstituted benzylglyoxals. The only method described so far for obtaining such α-keto aldehydes
has been a multi-step transformation of synthetically challenging α-cyano-α-hydroxymethyl epoxides.
This article describes a new, simple, and safe transformation based on the oxidation of readily available
sulfoxonium ylides under the action of Oxone. The reaction is carried out in a biphasic water-organic
solvent system, which greatly simplifies the isolation process. Short-path distillation of the obtained
oligomers provides a wide range of α-keto aldehydes.
Supplementary materials
Title
Supporting Information
Description
Supporting information includes analytical methods, a list of synthesized substrates, a description of the synthesis, and spectral data for the first three substrates for which the corresponding keto aldehyde was obtained, optimization tables (solvent, temperature, pH, stoichiometry, time), the synthesis methodology with detailed comments, as well as photographs of the process and spectral data (NMR and GC-MS spectra) for the first three α-keto aldehydes obtained through this new reaction.
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Title
TOC
Description
The picture showing the described reaction
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