Issue 8, 2021

Copper-catalyzed Goldberg-type C–N coupling in deep eutectic solvents (DESs) and water under aerobic conditions

Abstract

An efficient and selective N-functionalization of amides is first reported via a CuI-catalyzed Goldberg-type C–N coupling reaction between aryl iodides and primary/secondary amides run either in Deep Eutectic Solvents (DESs) or water as sustainable reaction media, under mild and bench-type reaction conditions (absence of protecting atmosphere). Higher activities were observed in an aqueous medium, though the employment of DESs expanded and improved the scope of the reaction to include also aliphatic amides. Additional valuable features of the reported protocol include: (i) the possibility to scale up the reaction without any erosion of the yield/reaction time; (ii) the recyclability of both the catalyst and the eutectic solvent up to 4 consecutive runs; and (iii) the feasibility of the proposed catalytic system for the synthesis of biologically active molecules.

Graphical abstract: Copper-catalyzed Goldberg-type C–N coupling in deep eutectic solvents (DESs) and water under aerobic conditions

Supplementary files

Article information

Article type
Paper
Submitted
15 dec 2020
Accepted
29 jan 2021
First published
29 jan 2021

Org. Biomol. Chem., 2021,19, 1773-1779

Copper-catalyzed Goldberg-type C–N coupling in deep eutectic solvents (DESs) and water under aerobic conditions

L. Cicco, J. A. Hernández-Fernández, A. Salomone, P. Vitale, M. Ramos-Martín, J. González-Sabín, A. Presa Soto, F. M. Perna, V. Capriati and J. García-Álvarez, Org. Biomol. Chem., 2021, 19, 1773 DOI: 10.1039/D0OB02501A

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