Unactivated C(sp(3))-H hydroxylation through palladium catalysis with H2O as the oxygen source.

A novel palladium catalyzed hydroxylation of unactivated aliphatic C(sp(3))-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.