Synthesis and Structure of Hypervalent Diacetoxybromobenzene and Aziridination of Olefins with Imino-位3-bromane Generated in Situ under Metal-Free Conditions

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• 作者：Md. Mahbubul Hoque ; Kazunori Miyamoto ; Norihiro Tada ; Motoo Shiro ; Masahito Ochiai
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：October 21, 2011
• 年：2011
• 卷：13
• 期：20
• 页码：5428-5431
• 全文大小：726K
• 年卷期：v.13,no.20(October 21, 2011)
• ISSN：1523-7052

文摘

Ligand exchange of p-CF₃C₆H₄BrF₂ with acetoxy groups using AcOH and Ac₂O affords (diacetoxybromo)benzene in a high yield, which undergoes aziridination of alkenes in the presence of TfNH₂ and sulfamate esters in one pot under mild conditions. The aziridination with TfNH₂ proceeds stereospecifically with retention of stereochemistry of olefins at room temperature using limiting amounts of olefins under transition-metal-free conditions. The one-pot aziridination procedure using sulfamate esters can be applied to the intramolecular versions.