Efficient Method for Aromatic‐Aldehyde Oxidation by Cleavage of Their Hydrazones Catalysed by Trimethylsilanolate. Issue 2 (13th January 2017)

• Record Type: Journal Article
• Authors: Burglova, Kristyna; Okorochenkov, Sergei; Budesinsky, Milos; Hlavac, Jan
• Is Part Of: European journal of organic chemistry. Issue 2(2017)
• Page Start: 389
• Page End: 396
• Publication Date: 2017-01-13
• Subjects: Aldehydes -- Oxidation -- Hydrazones -- Solid‐phase synthesis -- Reaction mechanisms; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601238
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The reactions of hydrazones, derived from various aromatic aldehydes bound to Rink resin and hydrazines, with trimethylsilanolate have been studied. In this process, the aldehydes were oxidized to the corresponding carboxylic acids. The reaction was also tested with success in solution, with various aromatic aldehydes easily being oxidized in one pot via hydrazone formation and trimethylsilanolate treatment. A mechanism for the hydrazone cleavage is proposed. The reaction may be used as an alternative method for aldehyde oxidation with the selectivity complementary to that of currently used reactions. Abstract : Aromatic aldehydes can be efficiently oxidized to the corresponding carboxylic acids. The protocol involves two reaction steps in one pot. First, an aldehyde is transformed into a hydrazone by reaction with phenylhydrazine, and is subsequently treated with trimethylsilanolate to yield a carboxylic acid. The oxidation can be performed both in solution and on a solid support.