Accessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation
John M Ovian1, Christopher B Kelly1, Vincent A Pistritto1
1Department of Chemistry, University of Connecticut , 55 North Eagleville Road, Storrs, Connecticut 06268, United States.
Abstract:
An operationally simple, robust, metal-free approach to the synthesis of N-acyl azoles from both alcohols and aldehydes is described. Oxidative amidation is facilitated by a commercially available organic oxidant (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and proceeds under very mild conditions for an array of structurally diverse substrates. Tandem reactions of these activated amides, such as transamidation and esterification, enable further elaboration. Also, the spent oxidant can be recovered and used to regenerate the oxoammonium salt.
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