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.
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.
W. Q. Tian, Y. A. Wang, J. Org. Chem. 2004, 69, 4299. DOI
F. L. Lin, H. M. Hoyt, H. V. Halbeek, R. G. Bergman, C. R. Bertozzi, J. Am. Chem. Soc, 2005, 127, 2686. DOI
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