Guanidinium iodide/urea hydrogen peroxide-catalyzed azidation of β-dicarbonyl compounds with trimethylsilyl azide

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• 作者：Koji Yasui ; ^{kyasui@cc.tuat.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Kohei Kojima ; Takanari Kato ; Minami Odagi ; Masaru Kato ; Kazuo Nagasawa ; ^{knaga@cc.tuat.ac.jp" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Guanidinium iodide ; Hypoiodite ; Azidation ; Metal-free reaction ; C&ndash ; H functionalization
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：1 September 2016
• 年：2016
• 卷：72
• 期：35
• 页码：5350-5354
• 全文大小：550 K

文摘

We present an efficient synthesis of α-azido-β-dicarbonyl compounds from β-dicarbonyl compounds and trimethylsilyl azide, catalyzed by guanidinium hypoiodite. The reaction can be run in air at ambient temperature (up to 40 °C) and is not sensitive to moisture. The substrate scope is broad, including cyclic and linear β-dicarbonyl compounds, and the α-azide products are obtained in 55%–99% yield.