Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step
Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step
复制标题
DOI：
10.1021/acs.joc.0c03044
复制
发表时间：
2021-02-04
影响因子：
3.6
通讯作者：
Koide, Kazunori
中科院分区：
文献类型：
--
作者：
Chan, Wei Chuen;Vinod, Jincy K.;Koide, Kazunori
我们描述了一种可见光促进的氢原子和缩醛碳与各种缺电子烯烃的加成反应。在可见光照射下，1，3-二氧杂环戊烷在过硫酸盐和Ir催化剂的存在下转化为其自由基物种，然后与缺电子的烯烃反应。该反应通过自由基链机制进行，这是这类转化较少观察到的途径。实验和密度泛函理论研究证实了氢原子从1，3-二氧杂环戊烷到α-丙二酸基的转移。
We describe a visible-light-promoted addition of a hydrogen atom and an acetal carbon toward various electron-deficient alkenes. 1,3-Dioxolane is converted to its radical species in the presence of persulfate and an iridium catalyst upon visible light irradiation, which then reacts with electron-deficient alkenes. The reaction operates via a radical chain mechanism, a less commonly observed pathway for this class of transformation. Hydrogen atom transfer from 1,3-dioxolane to alpha-malonyl radicals is corroborated by experimental and density functional theory studies.