Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide
Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide
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DOI：
10.1021/jacs.8b06881
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发表时间：
2018-10-03
影响因子：
15
通讯作者：
Schmidt, Valerie A.
中科院分区：
文献类型：
--
作者：
Lardy, Samuel W.;Schmidt, Valerie A.
以亚磷酸三乙酯和N-羟基邻苯二甲酰亚胺为原料，研究了烯烃的分子间反马氏氢胺化反应。该方法容许宽范围的烯烃，包括乙烯基醚、硅烷和硫化物以及电子无偏的末端和内部烯烃。所得的N-烷基邻苯二甲酰亚胺可以容易地转化为相应的伯胺。机理探针表明，该过程是介导的亚磷酸酯促进自由基脱氧N-羟基邻苯二甲酰亚胺访问邻苯二甲酰亚胺自由基。
An intermolecular anti-Markovnikov hydroamination of alkenes has been developed using triethyl phosphite and N-hydroxyphthalimide. The process tolerates a wide range of alkenes, including vinyl ethers, silanes, and sulfides as well as electronically unbiased terminal and internal alkenes. The resultant N-alkylphthalimides can readily be transformed to the corresponding primary amines. Mechanistic probes indicate that the process is mediated via a phosphite promoted radical deoxygenation of N-hydroxyphthalimide to access phthalimidyl radicals.