Recent advances on deoximation: From stoichiometric reaction to catalytic reaction

Deoximation reaction is one of the most important transformations in organic synthesis and for fine chemical production. Since oximes are easily synthesized from carbonyl compounds and are stable compounds, this reaction can be used for protection-deprotection, purification, and characterization of carbonyl compounds in organic synthesis, especially for the synthesis of medicines as well as the natural products. Moreover, because many oximes can be synthesized from non-carbonyl starting materials, the deoximation reaction is also widely used in the production of many carbonyl-contained fine chemicals. Deoximation methods by using stoichiometric reagents are mature and can produce the related carbonyl products in very high yield with broad substrate application scopes. But for environment-protection consideration as well as the production cost controlling purpose in fine chemical industry, developing catalytic deoximation methods is the trend of the field and there are a series of references on this topic in recent years. This short review summarized recent advances on the development of deoximation methods from stoichiometric reaction to catalytic reaction and the mechanisms of some important transformations were discussed in detail for reader reference. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.