Everything about The Staudinger Reaction totally explained
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 reaction was invented by and named after
Hermann Staudinger.
An example of a Staudinger reduction is the
organic synthesis of this pinwheel compound :
Reaction mechanism
The
reaction mechanism centers around the formation of an
iminophosphorane through
nucleophilic addition of the
phosphine at the terminal nitrogen atom of the azide and expulsion of nitrogen:
This intermediate is then hydrolyzed in the second step to the
amine and
triphenylphosphine oxide.
Staudinger ligation
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 general schematic for the Staudinger ligation is shown below.
Applications
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 :
Further Information
Get more info on 'Staudinger Reaction'.
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