Photoredox-Catalyzed Radical-Radical Cross-Coupling of α-Ketoesters with Ethers: Access to Sterically Hindered α-Hydroxy Esters.

Abstract

We describe a photoredox catalysis method for synthesizing sterically hindered α-hydroxy esters from α-ketoesters and ethers through a radical-radical cross-coupling reaction. This approach utilizes commercially available Ir[dF(CF3)ppy]2(dtbbpy)PF6 as a photocatalyst and inexpensive and readily available nBu4NBr as a hydrogen atom transfer catalyst. Unactivated tetrahydrofuran and other ethers effectively react with various α-ketoesters to yield the desired products. The efficiency of this reaction is highlighted by its broad substrate scope, good functional group tolerance, and mild reaction conditions.