Selective Hydrolysis of Primary and Secondary Amides Enabled by Visible Light

Org Lett. 2023 May 5;25(17):2948-2952. doi: 10.1021/acs.orglett.3c00354. Epub 2023 Feb 28.

Abstract

Amide hydrolysis is a fundamentally important transformation in organic chemistry. Developing hydrolysis procedures under mild conditions with a broad substrate scope is desirable. Herein, by leveraging a photoresponsive auxiliary o-nitroanilide, we established a mild two-step protocol for the hydrolysis of primary and secondary amides. This protocol is driven by visible light irradiation at room temperature under neutral conditions, which tolerates numerous acid- and base-sensitive functional groups. Various drugs, natural product-, and amino acid-derived amides can be selectively hydrolyzed.