A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1, 3-dimethylimidazolinium hexafluorophosphate

…, N Tashiro, Y Shiratake, M Sando, T Okauchi

Index: Kitamura, Mitsuru; Kato, So; Yano, Masakazu; Tashiro, Norifumi; Shiratake, Yuichiro; Sando, Mitsuyoshi; Okauchi, Tatsuo Organic and Biomolecular Chemistry, 2014 , vol. 12, # 25 p. 4397 - 4406

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Citation Number: 16

Abstract

Organic azides were prepared from primary amines in high yields by a metal free diazo- transfer reaction using 2-azido-1, 3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N, N-dimethyl) aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic ...