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

Abstract

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.

Synthesis of Heterocyclic Compounds with Pyrimidine-4-carbaldehydes as Key Intermediates

“…An entirely unexpected reaction was observed when pyrimidine-4-carbaldehyde 6 was treated with zinc powder and potassium hydroxide in DMSO (Scheme 6 ). 26 Under these conditions, we wanted to prepare the homologous aldehyde IV (Scheme 6 , right-hand side), but, instead, the 6-(pyrimidin-4-yl)furo[3,2- d ]pyrimidin-7-ol derivative 26 was isolated as the major product in good yield. As a side reaction, decarbonylation of 6 leading to pyrimidine derivative 25 was observed.…”

Palladium complex supported on the surface of magnetic Fe3O4 nanoparticles: an ecofriendly catalyst for carbonylative Suzuki-coupling reactions

“…40,41 Many ketones are known and many of them are of great importance in industry and biology. 42 Ketones include many sugars (ketoses) and acetone (the smallest ketone). 43 Ketones are mostly used as solvents, especially in explosives, varnish, paint and fabric production industries.…”