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由氮中心自由基的β-断裂介导的α,β-二烷基酰肼的C-N键活化

C-N Bond Activation of ,-Dialkylacylhydrazines Mediated by β-Fragmentation of Nitrogen-Centered Radical.

作者信息

Zhang Yuxian, Zhang Shuwei, Sun Zheng, He Kaixuan, Chen Qian, Yuan Yu, Jia Xiaodong

机构信息

School of Chemistry & Chemical Engineering , Yangzhou University , Yangzhou , Jiangsu 225002 , China.

出版信息

J Org Chem. 2019 Nov 1;84(21):14202-14208. doi: 10.1021/acs.joc.9b01851. Epub 2019 Oct 9.

DOI:10.1021/acs.joc.9b01851
PMID:31545604
Abstract

In the presence of -butylnitrite and dioxygen, the C-N bond activation of ,'-dialkylacylhydrazines was realized, providing a series of -nitrosoacylhydrazines in high yields. Different from transition-metal and other radical catalysis, this reaction is mediated by a nitrogen-centered radical of the corresponding ,'-dialkylacylhydrazine and further β-fragmentation, which was supported by the mechanistic study.

摘要

在存在亚硝酸叔丁酯和氧气的情况下,实现了α,α'-二烷基酰肼的C-N键活化,以高产率提供了一系列亚硝基酰肼。与过渡金属和其他自由基催化不同,该反应由相应的α,α'-二烷基酰肼的氮中心自由基介导并进一步发生β-碎片化,机理研究支持了这一点。

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