Selective Hydrolysis of Primary and Secondary Amides Enabled by Visible Light

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.

Automated summary

By utilizing a photoresponsive auxiliary o-nitroanilide, a mild two-step protocol for the hydrolysis of primary and secondary amides has been developed. This protocol, driven by visible light irradiation at room temperature under neutral conditions, tolerates numerous acid-and base-sensitive functional groups. Various drugs, natural product-, and amino acid-derived amides can be selectively hydrolyzed.