4.7 Article

One-Step Synthesis of Arylacetaldehydes from Aryl Aldehydes or Diaryl Ketones via One-Carbon Extension by Using the System of DMSO/KOH/Zinc

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 17, Pages 2989-2995

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200437

Keywords

Arylacetaldehydes; Aryl aldehydes or Diaryl ketones; DMSO; KOH; One-Carbon Extension

Funding

  1. National Natural Science Foundation of China [21572049]

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A one-step protocol is developed for the synthesis of arylacetaldehydes from aryl aldehydes or diaryl ketones, providing a potential efficient method for organic synthesis.
A one-step protocol is described for the synthesis of arylacetaldehydes from aryl aldehydes or diaryl ketones by using the system of DMSO/KOH/zinc. In this transformation, DMSO provides a methine fragment that converts the -CHO structure in aryl aldehydes or the -CO- structure in diaryl ketones to the -CH2CHO structure in arylacetaldehydes via a one-carbon extension. This protocol could also be used to synthesize arylacetaldehyde acetals from aryl aldehydes or diaryl ketones when zinc was replaced by diols. In this protocol, 25 examples of arylacetaldehydes and 26 examples of arylacetaldehyde acetals have been synthesized from aryl aldehydes or diaryl ketones. Based on control experiments and the literature, a plausible reaction mechanism is proposed in our work.

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