Direct, one-pot reductive alkylation of anilines with functionalized acetals mediated by triethylsilane and TFA. Straightforward route for unsymmetrically substituted ethylenediamine

J Org Chem. 2011 Jan 21;76(2):704-7. doi: 10.1021/jo102109f. Epub 2010 Dec 22.

Abstract

A new, robust, and reliable method has been developed for the selective reductive N-alkylation of primary and secondary aromatic amines with some functionalized acetals using TFA/Et(3)SiH as a reagent combination. A variety of unsymmetrically substituted ethylenediamines can be synthesized in a one-pot procedure in excellent yields at room temperature. This new procedure offers significant advantages over previous synthetic approaches, including brevity, mild reaction conditions, excellent yields, and high functional group tolerance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry*
  • Alkylation
  • Aniline Compounds / chemistry*
  • Catalysis
  • Ethylenediamines / chemical synthesis*
  • Ethylenediamines / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Silanes / chemistry*
  • Trifluoroacetic Acid / chemistry*

Substances

  • Acetals
  • Aniline Compounds
  • Ethylenediamines
  • Silanes
  • triethylsilane
  • ethylenediamine
  • Trifluoroacetic Acid
  • aniline