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Issue 25, 2014
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A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate

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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 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.

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

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Article information


Submitted
07 Mar 2014
Accepted
29 Apr 2014
First published
29 Apr 2014

Org. Biomol. Chem., 2014,12, 4397-4406
Article type
Paper

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

M. Kitamura, S. Kato, M. Yano, N. Tashiro, Y. Shiratake, M. Sando and T. Okauchi, Org. Biomol. Chem., 2014, 12, 4397
DOI: 10.1039/C4OB00515E

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