Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes
Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes
复制标题
亚氨基自由基促进的二分环化：烯烃的有效氧肟化和氨基肟化
DOI：
10.1021/ol502258n
复制
发表时间：
2014-09-05
期刊：
影响因子：
5.2
通讯作者：
Han, Bing
中科院分区：
文献类型：
--
作者：
Peng, Xie-Xue;Deng, Yun-Jing;Han, Bing
发展了一种新的亚氨氧基自由基参与的未活化烯烃邻位氧肟化和氨肟化反应的无金属方法。该方法利用亚氨氧基自由基的二分反应性，使用简单的亚硝酸叔丁酯（TBN）作为亚氨氧基自由基引发剂以及碳自由基捕获剂，提供烯烃上的一般双官能化。利用该方法，分别从β，γ-和γ，δ-不饱和酮肟制备了肟特征的4，5-二氢异恶唑和环状硝酮。
A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from beta,gamma- and gamma,delta-unsaturated ketoximes, respectively.