Direct alkylative Passerini reaction of aldehydes, isocyanides, and free aliphatic alcohols catalyzed by indium(III) triflate

J Org Chem. 2009 May 15;74(10):3927-9. doi: 10.1021/jo900354e.

Abstract

In(OTf)(3) was found to be a useful Lewis acid catalyst for direct alkylative Passerini reaction of aldehydes, isocyanides, and free aliphatic alcohols. In the present reaction, aromatic and alpha,beta-unsaturated aldehydes performed as nice substrates to give the corresponding alpha-alkoxy amide products in good yield.

MeSH terms

  • Alcohols / chemistry*
  • Aldehydes / chemistry*
  • Alkylation
  • Catalysis
  • Cyanides / chemistry*
  • Mesylates / chemistry*

Substances

  • Alcohols
  • Aldehydes
  • Cyanides
  • Mesylates
  • trifluoromethanesulfonic acid