Transition-Metal-Free Coupling of Butadienes with Aldehydes

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  • Published: 14 September 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Transition-Metal-Free Coupling of Butadienes with Aldehydes

To synthesize homoallylic alcohols, organic chemists often perform allylations of aldehydes. The reductive coupling of conjugated butadienes with aldehydes is one possible approach for this. However, this reaction requires expensive transition-metal catalysts.

Ikuya Shibata and colleagues, Osaka University, Japan, have developed a transition-metal-free direct coupling of 1,3-butadienes with aldehydes. The team prepared the catalyst, dibutyliodotin hydride (Bu2SnIH), in situ by combining dibutyltin diiodide (Bu2SnI2) and dibutyltin dihydride (Bu2SnH2) in acetonitrile. Then, they added a butadiene derivative, an aldehyde, Ph2SiH2 as a hydride source, and methanol as an additive, and heated the reaction mixture to 25 °C for 24 hours.

The coupling reaction tolerates a wide range of aldehydes and various dienes and proceeds in moderate to good yields. The team proposes a radical reaction mechanism, since radical scavengers inhibit the reaction. According to the researchers, the reaction could be a suitable alternative to the use of transition-metal catalysts for coupling dienes and aldehydes.


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