Staudinger Reaction
Staudinger Reduction
Azides may be converted to amines by hydrogenation, but another possibility is the Staudinger Reaction, which is a very mild azide reduction. As there are a variety of methods for preparing azides readily, the Staudinger Reaction makes it possible to use -N3 as an -NH2 synthon.
Mechanism of the Staudinger Reaction
Triphenylphosphine reacts with the azide to generate a phosphazide, which loses N2 to form an iminophosphorane. Aqueous work up leads to the amine and the very stable phosphine oxide.
Recent Literature
Catalytic Staudinger Reduction at Room Temperature
A One-Pot, Solid-Phase Synthesis of Secondary Amines from Reactive Alkyl Halides and an Alkyl Azide
ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis
Catalytic Staudinger-Vilarrasa Reaction for the Direct Ligation of Carboxylic Acids and Azides
One-Pot Synthesis of Polysubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Ag(I)-Catalyzed Cyclization/Isomerization
Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy
A Tandem Approach to Isoquinolines from 2-Azido-3-arylacrylates and α-Diazocarbonyl Compounds
Three-Component, One-Pot Sequential Synthesis of 1,3-Disubstituted 5-Arylhydantoins
Staudinger Condensation for the Preparation of Thiohydantoins
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