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

作者：Kitamura Mitsuru^*; Kato So; Yano Masakazu; Tashiro Norifumi; Shiratake Yuichiro; Sando Mitsuyoshi; Okauchi Tatsuo

来源：Organic and Biomolecular Chemistry, 2014, 12(25): 4397-4406.

DOI：10.1039/c4ob00515e

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 primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses.

• 出版日期2014