Unactivated C(sp3)–H hydroxylation through palladium catalysis with H2O as the oxygen source

Abstract

A novel palladium catalyzed hydroxylation of unactivated aliphatic C(sp³)–H bonds was successfully developed. Different from conventional methods, water serves as the hydroxyl group source in the reaction. This new reaction demonstrates good reactivity and broad functional group tolerance. The C–H hydroxylated products can be readily transformed into various highly valuable chemicals via known transformations. Based on experimental and theoretical studies, a mechanism involving the Pd(II)/(IV) pathway is proposed for this hydroxylation reaction.