Aza-Wittig Reaction

Aza-Wittig Reaction

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  • Generality
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  • Application to Chemical Biology
  • General Characteristics

Nucleophilic phosphorus reagents such as triphenylphosphine react with azides to generate, via the Staudinger reaction, N-P ylide (iminophosphorane) intermediates, which react with carbonyl compounds to produce imines. Therefore, this reaction is considered the nitrogen version of the Wittig reaction.

  • General References

Shah, S.;Protasiewicz,J. D. Coord. Chem. Rev. 2000, 210, 181. doi:10.1016/S0010-8545(00)00311-8

Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G;  M. de los Santos, J. M. Tetrahedron, 2007, 63, 523. DOI: 10.1016/j.tet.2006.09.048

  • History

In 1919, Staudinger and Myers reported that azides and phosphines reacted to form N-P ylides, which could be converted to amines after hydrolysis (the Staudinger reaction). About 30 years later, it was demonstrated that the N-P ylides could react with carbonyl compounds to give imines. This and related reactions are called the aza-Wittig reaction.

  • Reaction Mechanism


  • Examples

Iminophosphoranes can react with a variety of electrophiles to give the corresponding products, as summarized below.


An application to the synthesis of a secondary amine.


  • Experimental Procedure

  • Experimental Tips

  • References

  • Related Reactions

Bode Peptide Synthesis

Staudinger Reaction

Horner-Wadsworth-Emmons (HWE) Reaction

Wittig Reaction

  • Related Books

  • External Links

Bertozzi ResearchGroup (UC Berkeley)

A New way to Engineer Cells: The Staudinger Ligation: Chemoselective, mild, and high-yielding chemical ligation based on the Staudinger reaction.

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