Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions

In this work, a visible-light-induced oxidative alpha-alkylation of glycine derivatives with ethers has been developed in the presence of catalytic Eosin Y. Under the blue light of a 3 W LED, a range of alpha-etherized glycine derivatives, including alpha-amino esters, alpha-amino ketones and alpha-amino amides, were achieved with good to excellent yields and functional group tolerance with tert-butyl hydroperoxide (TBHP) as oxidant at ambient temperature. The operationally easy procedure provides an economical, metal-free, and mild alternative for the synthesis of the alpha-etherized glycine derivatives.

Automated summary

This work presents a visible-light-induced oxidative alpha-alkylation of glycine derivatives with ethers using Eosin Y as a catalyst. The reaction, conducted under blue light from a 3 W LED, produces a range of alpha-etherized glycine derivatives with good to excellent yields and functional group tolerance when tert-butyl hydroperoxide is used as the oxidant at ambient temperature. This operationally easy procedure offers an economical, metal-free, and mild approach for synthesizing alpha-etherized glycine derivatives.