Alcohol Etherification Via Alkoxy Radicals Generated By Visible-Light Photoredox Catalysis

A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1 degrees, 2 degrees, and 3 degrees alcohols and allows their use in the functionalization of C(sp(3))-H and C(sp(2))-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.