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Boronic Acid‐Catalyzed Selective Oxidation of 1,2‐Diols to α‐Hydroxy Ketones in Water
Author(s) -
William Julius M.,
Kuriyama Masami,
Onomura Osamu
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300961
Subject(s) - chemistry , bromide , electrochemistry , catalysis , aqueous solution , boronic acid , diol , anode , platinum , combinatorial chemistry , organic chemistry , inorganic chemistry , electrode
The activation of 1,2‐diols through formation of boronate esters was found to enhance the selective oxidation of 1,2‐diols to their corresponding α‐hydroxy ketones in aqueous medium. The oxidation step was accomplished using dibromoisocyanuric acid (DBI) as a terminal chemical oxidant or an electrochemical process. The electrochemical process was based on the use of platinum electrodes, methylboronic acid [MeB(OH) 2 ] as a catalyst and bromide ion as a mediator. Electro‐generated OH − ions (EGB) at the cathode acted as a base and “Br + ” ion generated at the anode acted as an oxidant. Various cyclic and acyclic 1,2‐diols as substrates were selectively oxidized to the corresponding α‐hydroxy ketones via their boronate esters by the two oxidative methods in good to excellent yields.