Direct Synthesis of 1,4-Diols from Alkenes by Iron-Catalyzed Aerobic Hydration and C-H Hydroxylation

Various 1,4-diols are easily accessible from alkenes through iron-catalyzed aerobic hydration. The reaction system consists of a user-friendly iron phthalocyanine complex, sodium borohydride, and molecular oxygen. Furthermore, the effect of additional ligands on the iron complex was examined for a model reaction. The second hydroxy group is installed by direct C(sp(3))H oxygenation, which is based on a [1,5]hydrogen shift process of a transient alkoxy radical that is formed by formal hydration of the olefin.