Issue 27, 2022

Eosin-Y/Cu(OAc)2-catalyzed aerobic oxidative coupling reactions of glycine esters in the dark

Abstract

Catalytic aerobic oxidative coupling reactions of glycine esters with β-keto acids, indoles, naphthols, and pyrrole have been realized at ambient temperature via the manipulation of the ground state reactivity of eosin-Y in the presence of Cu(OAc)2 in the dark. This method delivers structurally diverse unnatural amino acid derivatives under mild reaction conditions. UV-vis absorption spectroscopy, cyclic voltammetry, X-ray photoelectron spectroscopy, high-resolution mass spectrometry, and control experiments were performed to formulate a plausible mechanistic pathway. The step economy, broad substrate scope, use of air as a green oxidant, and operationally simple set-up make this protocol highly appealing for both academic and industrial applications.

Graphical abstract: Eosin-Y/Cu(OAc)2-catalyzed aerobic oxidative coupling reactions of glycine esters in the dark

Supplementary files

Article information

Article type
Communication
Submitted
10 Apr 2022
Accepted
15 Jun 2022
First published
16 Jun 2022

Org. Biomol. Chem., 2022,20, 5387-5392

Eosin-Y/Cu(OAc)2-catalyzed aerobic oxidative coupling reactions of glycine esters in the dark

R. Chowdhury, Org. Biomol. Chem., 2022, 20, 5387 DOI: 10.1039/D2OB00678B

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