Electrochemical hydroxylation of organoboron compounds

Abstract

Cathodic hydroxylation of organoboron compounds was successfully performed under an oxygen atmosphere, producing the corresponding phenol derivatives with high selectivity and efficiency.

Contributions of organic electrosynthesis to green chemistry

“…Presumably molecular oxygen is reduced to the anion radical that substitutes one hydroxy group and after reduction to the peroxy anion induces the rearrangement of the aryl group to oxygen. Hydrogen peroxide and KO 2 react with lower yield and selectivity [94].…”

Boron chemistry in a new light

“…42 In addition, few among them are sustainable processes. In order to address these limitations, the Jørgensen and the Xiao groups developed a highly efficient visible-light-mediated photoredox strategy relying on the utilization of oxygen from ambient air as the terminal oxidant.…”

Aerobic photooxidative hydroxylation of boronic acids catalyzed by anthraquinone-containing polymeric photosensitizer

“…Oxidative hydroxylation of boronic acids is one of the most important methods for the synthesis of phenols or alcohols. [1][2][3][4][5][6][7] Strong oxidants such as ozone, 8 high-valence halogen compounds, [9][10][11] peroxides and N-oxides 12 are efficient reagents for such transformations (Scheme 1a). However, these methods generate large amounts of wastes detrimental to the environment.…”