A New Reaction of Togni Reagent II: α-C–H Ester-Functionalization of Tertiary Amides

29 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Togni reagent II is a synthetically useful hypervalent iodine reagent for direct trifluoromethylation. Herein, we report a new reaction of Togni reagent II: α-C–H ester-functionalization of tertiary amides. This α-acyloxylation reaction proceeds smoothly in the presence of a mild base at 25–30 oC and produces moderate-to-high yields. This newly discovered reaction adds another dimension to the utility of Togni reagent II and provides direct and easy access to α-acyloxy amides and α-hydroxy amides.

Keywords

Togni reagent II
α-C–H ester-functionalization
benzoyloxylation
α-acyloxy amides
α-hydroxy amides

Supplementary materials

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Supporting Information
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Experimental procedures, full characterization of all prepared compounds, and copies of all spectral data.
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