Visible-Light-Promoted Carboimination of Unactivated Alkenes for the Synthesis of Densely Functionalized Pyrroline Derivatives
Visible-Light-Promoted Carboimination of Unactivated Alkenes for the Synthesis of Densely Functionalized Pyrroline Derivatives
复制标题
可见光促进未活化烯烃的碳亚胺化用于合成稠密功能化吡咯啉衍生物
DOI：
10.1021/acscatal.6b01230
复制
发表时间：
2016-08-01
期刊：
影响因子：
12.9
通讯作者：
Loh, Teck-Peng
中科院分区：
文献类型：
--
作者：
Cai, Sai-Hu;Xie, Jia-Hao;Loh, Teck-Peng
已经开发了一种有效的策略，该策略将可见光诱导的亚米氨基激气形成与未活化的烯烃的碳水化合物结合在一起，以方便地访问密集的功能化的吡咯烷衍生物。用fac- [ir（ppy）（3）]作为光毒催化剂，将酰基氧通过一个电子还原转化为氨基氨基自由基中间体，并通过一系列分子内环化和分子间碳自由基捕获的级联进化，从而获得了官能的吡咯酸酯。 Silyl Enol Ethers作为耦合伙伴的利用不仅允许引入合成有用的酮功能，而且还可以使催化剂再生无需任何外部还原剂。该方案的特征是其轻度的反应条件和广泛功能的耐受性。
An efficient strategy which integrates visible-light-induced iminyl-radical formation with carboimination of unactivated alkenes has been developed for the easy access of densely functionalized pyrroline derivatives. With fac-[Ir(ppy)3] as photoredox catalyst, the acyl oximes were converted into iminyl radical intermediates by one electron reduction, and evolve through a cascade of intramolecular cyclization and intermolecular carbon radical trapping to give the functionalized pyrrolines. The utilization of silyl enol ethers as coupling partners not only allows the introduction of synthetically useful ketone functionalities but also renders catalyst regeneration without any external reductants. This protocol is characterized by its mild reaction conditions and the tolerance of a broad range of functionalities.