化学
烯烃
共价键
光化学
区域选择性
共轭体系
三苯胺
电子供体
光催化
双键
键裂
共价有机骨架
有机化学
组合化学
催化作用
光催化
聚合物
作者
Anupam Das,Karampreet Kaur,K. R. Justin Thomas
标识
DOI:10.1021/acs.joc.3c01594
摘要
The conversion of alkenes to carbonyl constituents via the cleavage of the C═C bond is unique due to its biological and pharmacological significance. Though a number of oxidative C═C cleavage protocols have been demonstrated for terminal and electron-rich alkene systems, none of them were optimized for electron-deficient and conjugated alkenes. In this work, a covalent organic framework containing triphenylamine and triazine units was revealed to cleave the C═C bond of alkenes under very mild conditions involving visible light irradiation due to its photoredox property. The alkenes can be conveniently broken across the double bond to their constituent carbonyl derivatives on light irradiation in the presence of air and the covalent organic framework photocatalyst. This protocol is applicable for a wide range of alkenes in an aqueous acetonitrile medium with high functional group tolerance and regioselectivity. Though the electron-deficient alkenes required tetramethylethylene diamine as a sacrificial donor, the electron-rich alkenes do not demand any additives.
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