The Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces an aza-ylide intermediate . Combined with the hydrolysis of the aza-ylide to produce a phosphine oxide and an amine, this reaction is a mild method of reducing an azide to an amine. The reaction was invented by and named after Hermann Staudinger. Developed by Saxon and Bertozzi in 2000, the Staudinger ligation is a modification of the classical Staudinger reaction in which an electrophilic trap (usually a methyl ester) is appropriately placed on the triaryl phosphine. In the Staudinger ligation, the aza-ylide intermediate rearranges, in aqueous media, to produce an amide linkage and the phosphine oxide, and is so named the Staudinger ligation because it ligates the two molecules together, whereas in the classical Staudinger reaction, the two products are not covalently linked after hydrolysis. The Staudinger ligation has seen many applications in the field of chemical biology.

An example of a Staudinger reduction is the organic synthesis of this pinwheel compound :

The general schematic for the Staudinger ligation is shown below.

Reaction mechanism

References

1. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
2. Gololobov, Y. G. et al. Tetrahedron 1981, 37, 437.
3. Saxon, E.; Bertozzi, C.R. Science 2000, 287, 2007.
4. Preparation of 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene from Two Versatile 1,3,5-Tri(halosubstituted) 2,4,6-Triethylbenzene Derivatives Karl J. Wallace, Robert Hanes, Eric Anslyn, Jeroni Morey, Kathleen V. Kilway, Jay Siegeld Synthesis 2005: 2080-2083. (Abstract)

Organic reactions