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讲准字15号:Azidoimidazolinium Salts: Safe and Efficient Diazo-transfer Reagents and Unique Azido-donors

发布时间:2018-03-01|浏览次数:

题目:Azidoimidazolinium Salts: Safe and Efficient Diazo-transfer Reagents and Unique Azido-donors

主讲:Mitsuru Kitamura

时间:2018年3月8日 10:30

地点:化学化工学院212报告厅

主办:化学化工学院


主讲简介:Mitsuru Kitamura,日本九州工业大学教授。研究专长:有机合成化学。日本庆应大学学士,东京工业大学化学博士,日本JSPS青年学者。先后获得日本学术振兴会青年科学家奖、日本青年科学家前沿研究奖、日本化学会通报奖、日本化学会青年化学家奖、日本合成有机化学会奖等多项奖励。分别在Chem. Commun.,J. Org. Chem.,Eur. J. Org. Chem.等国际知名刊物发表论文100余篇。

主讲内容:2-Azido-1,3-dimethylimidazolinium chloride (ADMC) and its corresponding hexafluorophosphate (ADMP) were found to be efficient diazo-transfer reagents to various organic compounds. ADMC was prepared by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium azide. ADMP was isolated as a crystal having good thermal stability and low explosibility. ADMC and ADMP reacted with 1,3-dicarbonyl compounds under mild basic conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which were easily isolated in virtue of the high water solubility of the by-products. ADMP showed high diazo-transfer ability to primary amines even in the absence of metal salt such as Cu(II). Using this diazotization approach, various alkyl/aryl azides were directly obtained from their corresponding primary amines in high yields. Furthermore, naphthols reacted with ADMC to give the corresponding diazonaphthoquinones in good to high yields. In addition, 2-azido-1,3-dimethylimidazolinium salts were employed as azide-transfer and migratory amidation reagents.


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