Ioanna Sideri

Green PhotoOrganocatalytic Synthesis of Phenols from Arylboronic Acids

The Laboratory of Organic Chemistry of the University of Athens has developed a photoorganocatalytic protocol for various radical transformations utilizing phenylglyoxylic acid as the photoorganocatalyst.^[1-4] Herein, the aim was to develop an efficient, economic, green and easy way to convert aryl boronic acids into phenols utilizing a cheap, small organic molecule as the photocatalyst, water as the solvent and household bulbs as means of irradiation. 2,2-Dimethoxy-2-phenylacetophenone proved to be the best photoinitiator, among a range of organocalalysts in promoting this reaction. This photocatalytic protocol can be expanded into a wide substrate scope of aromatic boronic acids bearing various functional groups, leading to the corresponding phenols in good to high yields under mild reaction conditions, which include water as  solvent, light irradiation provided from household bulbs, room temperature and air as the oxidant.^[4]

[1] G. N. Papadopoulos, D. Limnios, C. G. Kokotos, Chem. Eur. J., 2014, 20, 13811-13814.
[2] G. N. Papadopoulos, C. G Kokotos, Chem. Eur. J., 2016, 22, 6964-6967.
[3] G. N. Papadopoulos, C. G. Kokotos, J. Org. Chem., 2016, 81, 7023–7028.
[4] D. Limnios, C. G. Kokotos, Adv. Synth. Catal., 2017, 359, 323-328.
[5] I. K. Sideri, E. Voutyritsa, C. G. Kokotos, Synlett, 2018, DOI: 10.1055/s-0036-1591837.