Sodium Azide (NaN3): A Versatile Reagent in Organic Synthesis

Abstract

Sodium azide is a colorless, odorless, white crystalline solid, which is commercially available and widely used in industry, agriculture, medical practice, and organic ­transformations. It has been used for synthesis of β- and γ-azidoarylketones, [1] dialkylcarbamoyl azides, [2] diphen­ylphosphoryl azides, [3] acyl azides, [4] aryl azides, [5] allyl azides, [6] 1,5-fused tetrazoles, [7] 5-substituted 1H-tetrazoles, [8] 1,2,3-triazoles, [9] 1-aryl 1,2,3-triazoles, [10] 1,4-disubstituted 1,2,3-triazoles, [11] and 1-N-glycosylthio­methyl-1,2,3-triazoles. [12] In addition, sodium azide has been widely employed for preparation of α-azido­ketones, [13] 1-aryl-1H-benzotriazoles, [14] 3-cyanoindoles, [15] and Fmoc-protected amino alcohols, [16] as a suitable ­nucleophile for the Michael-induced ring closure of 2-bromoalkylidene­malonates to 3,3-dialkyl-2-azidocyclopropane-1,1-dicarboxylates. [17]