An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate
An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate
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DOI：
10.1021/acs.joc.6b00177
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发表时间：
2016-04-15
影响因子：
3.6
通讯作者：
Gardiner, John M.
中科院分区：
文献类型：
--
作者：
Potter, Garrett T.;Jayson, Gordon C.;Gardiner, John M.
咪唑-1-磺酰叠氮及其盐是用于重氮基转移反应，最特别是伯胺转化为叠氮化物的有价值的试剂。母体试剂及其HCl盐存在稳定性和爆炸风险，但硫酸氢盐明显更稳定。用于大规模合成该盐的更新程序避免了母体化合物或HCl盐的分离或浓缩，并且将促进使用硫酸氢盐作为重氮转移的选择试剂。
Imidazole-1-sulfonyl azide and salts thereof are valuable reagents for diazo-transfer reactions, most particularly conversion of primary amines to azides. The parent reagent and its HCl salt present stability and detonation risks, but the hydrogen sulfate salt is significantly more stable. An updated procedure for the large-scale synthesis of this salt avoids isolation or concentration of the parent compound or HCl salt and will facilitate the use of hydrogen sulfate salt as the reagent of choice for diazo transfer.