K₂S₂O₈-mediated nitration of alkenes with NaNO₂ and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of (E)-nitroalkenes

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• 作者：An Zhao ; Qing Jiang ; Jing Jia ; Bin Xu ; Yufeng Liu ; Mingzhong Zhang ; Qiang Liu ; Weiping Luo ; Cancheng Guo ; ^{ccguo@hnu.edu.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Persulfate salts ; Nitration ; Alkenes ; Stereoselective ; Nitroalkenes
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：6 January 2016
• 年：2016
• 卷：57
• 期：1
• 页码：80-84
• 全文大小：1068 K

文摘

A transition-metal-free nitration of alkenes with NaNO₂ in the presence of K₂S₂O₈ and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) is developed. The transformation exhibits a broad substrate scope and good functional group tolerance, thus providing a new and expedient protocol for stereoselective synthesis of (E)-nitroalkenes with moderate to good yields. Moreover, the nitration processes of (E)- and (Z)-stilbene are also studied: even though the proportion of substrates is different, the E/Z ratio of the products is basically the same. Based upon experimental observations, a possible reaction mechanism is proposed.