Cobalt-Catalyzed Chemoselective Isomerization of 2-Substituted Allyl Ethers Induced by Hydrogen Atom Transfer

A simple, mild and efficient method for the isomerization of 2-substituted allyl ethers has been developed by cobalt-catalyzed hydrogen atom transfer (HAT) process. The trivalent cobalt complex oxidized in-situ by tert-butyl hydroperoxide (tBuOOH) exhibits higher catalytic activity than prefabricated trivalent cobalt catalysts. This facile protocol displays excellent chemoselectivity, good functional group tolerance and high yields. The obtained vinyl ethers can be easily hydrolyzed by N-iodosuccinimide/water to afford corresponding phenols or alcohols.

Automated summary

A simple, mild, and efficient method for the isomerization of 2-substituted allyl ethers has been developed using a cobalt-catalyzed hydrogen atom transfer process. The in-situ oxidized trivalent cobalt complex by tert-butyl hydroperoxide exhibits higher catalytic activity compared to prefabricated cobalt catalysts. This protocol shows excellent chemoselectivity, good functional group tolerance, and high yields.