This is a tutorial on the Staudinger/aza-Wissig reaction.The Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces an iminophosphorane 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. Triphenylphosphine is commonly used as the reducing agent, yielding triphenylphosphine oxide as the side product in addition to the amine.



The Staudinger ligation has seen many applications in the field of chemical biology.In one application this reaction is used to create a bond between a nucleoside and a fluorescent marker.