Research Highlights

Synthesis: No harmful substances needed

Subject Categories: Chemistry

Published online 5 March 2014

doi:10.1038/nchina.2014.13

Researchers in Guangzhou report an eco-friendly method for synthesizing sulfone derivatives

Felix Cheung

© (2014) Wiley Interscience

The alkylation of phenacyl halides with sodium sulfinates (see top equation) is the conventional method for preparing sulfone derivatives — synthetic intermediates widely used in the construction of natural products. However, the coupling reaction generally requires the use of expensive transition-metal catalysts and toxic oxidants, such as iodobenzene diacetate and hydrogen peroxide.

Now, Huanfeng Jiang and co-workers at the South China University of Technology in Guangzhou have reported a copper-catalysed coupling reaction that yields sulfonylvinylamine products from oxime acetates and sodium sulfinates (see bottom equation). Because the oxime acetates serve as both substrates and internal oxidants, the coupling reaction does not require any additional oxidants.

The researchers first carried out the coupling reaction of acetophenone oxime acetate with sodium p-toluenesulfinate in the presence of copper iodide and toluene at 100 °C. By optimizing the conditions of the coupling reaction, they could achieve a product yield as high as 77%.

The researchers then explored the possibilities of substituting acetophenone oxime acetate with other oxime acetates in the coupling reaction. In nearly all cases, the coupling reaction gave excellent product yields of between 72% and 95%. This result is great news for industries that use sulfone derivatives.

The authors of this work are from:
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China.


Reference

  1. Tang, X. et al. Copper-catalyzed coupling of oxime acetates with sodium sulfinates: an efficient synthesis of sulfone derivatives. Angew. Chem. Int. Ed. 10.1002/anie.201311217 (2014). | Article |