Phenol moieties are found in a wide variety of bioactive molecules and pharmaceuticals. Throughout the synthesis of these compounds, protecting groups are often employed to prevent side reactions caused by these acidic functional groups. Benzylation of phenols into their corresponding ethers is one of the most common approaches due to the high stability of the resulting C–O bond. Traditional deprotect these phenol ethers is often performed via hydrogenation reactions or through the oxidative processes, which are incompatible with many functional groups, including alkenes. Herein, we present a mild and efficient light-mediated deprotection methodology to enable the cleavage of C–O bonds via an electron-donor-acceptor complex. The reaction proceeds using only base in a variety of solvents. Mechanistic work suggests that the reaction takes place via a single electron reduction process. Substrate scope, and mechanistic investigation will be presented.

Catalyst-free light mediated reductive dealkylation of phenol ethers

Where thousands of chemistry professionals meet to share ideas and advance scientific and technical knowledge. Spring 2023 abstracts, posters, and presentations will launch at the end of March.

ACS Spring 2023

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.