IBS-Catalyzed Regioselective Oxidation of Phenols to 1,2-Quinones with Oxone®

Molecules

Muhammet Uyanik¹  Tatsuya Mutsuga¹ 

[1] ¹Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan ²Japan Science and Technology Agency (JST), CREST, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan

关键词: xidation;    phenol;    o-quinone;    2-iodoxybenzenesulfonic acid (IBS);    Oxone^®;   

DOI  :  10.3390/molecules17078604

来源: mdpi

【 摘 要 】

We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone^® as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K₂CO₃), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu₄NHSO₄), and a dehydrating agent such as anhydrous sodium sulfate (Na₂SO₄).

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.