A self-sufficient method for the one-pot conversion of aldehydes to carboxylic acid derivatives has been developed.  This method achieves direct anodic oxidation of catalytically-generated Breslow intermediates by using a combination of NHC-based organocatalysis and electro-organic synthesis that may be termed electro-organocatalysis (EOC).  By employing EOC to achieve the redox transformation, exogenous oxidants, transition metal reagents, stoichiometric installation of electroauxiliaries, and harsh oxidation potentials are avoided while producing H2 gas as the only byproduct. We have expanded the scope of EOC to include the one-pot conversion of aldehydes to thioesters.  The design of novel thiazolinium precatalysts and the redox properties of azolium salts will also be discussed.

Interfacing NHC-based organocatalysis with electro-organic synthesis for the conversion of aldehydes to carboxylic acid derivatives

247th National Meeting (2014)

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