ChemInform Abstract: A Reagent for Safe and Efficient Diazo‐Transfer to Primary Amines: 2‐Azido‐1,3‐dimethylimidazolinium Hexafluorophosphate.

Abstract

A Reagent for Safe and Efficient Diazo-Transfer to Primary Amines: 2-Azido--1,3-dimethylimidazolinium Hexafluorophosphate. -The title compound, a safe, crystalline, and commercially available substance, is found to be an efficient diazo--transfer reagent for primary amines, even without the aid of a metal salt such as Cu(II). Various alkyl and aryl azides (II), (IV), and (VI) are obtained directly from the corresponding amines (I), (III), and (V). The choice of base is important in the diazo-transfer reaction. In general DMAP is efficient, but stronger bases such as alkylamine of DBU are more appropriate for the reaction of nucleophilic primary amines. -(KITAMURA*, M.; KATO, S.; YANO, M.; TASHIRO, N.; SHIRATAKE, Y.; SANDO, M.; OKAUCHI, T.; Org. Biomol. Chem. 12 (2014) 25, 4397-4406, http://dx.doi.org/10.1039/c4ob00515e ; Dep. Appl. Chem., Fac. Eng., Kyushu Inst. Technol., Tobata, Kitakyushu 804, Japan; Eng.) -M. Paetzel 48-039