Donor-Acceptor Covalent Organic Frameworks as a Heterogeneous Photoredox Catalyst for Scissoring Alkenes to Carbonyl Constituents

The conversion of alkenes to carbonyl constituents via the cleavage of the (CC)-C-= bond is unique due to its biological and pharmacological significance. Though a number of oxidative (CC)-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 (CC)-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.

Automated summary

This study discovered a covalent organic framework that can cleave the (CC)-C-= bond of alkenes under light irradiation and convert them into their constituent carbonyl derivatives. The method is applicable for a wide range of alkenes and has high functional group tolerance and regioselectivity.