Issue 3, 2024

Rational design of galactopyranoside-substituted N-heterocyclic carbene palladium(ii) complexes. Stable and efficient catalyst for C–C coupling in aqueous media

Abstract

Following a rational design, three novel palladium(II) complexes bearing galactopyranoside-based N-heterocyclic carbene ligands have been synthesized via transmetalation of the corresponding Ag(I) complexes. Palladium(II) complexes have been characterized by NMR, FT-IR and elemental analysis. Catalytic studies, using the Stille and Suzuki–Miyaura cross-coupling reactions as model C–C coupling, reveal that the complexes are active and reusable. The best results in terms of TON values were achieved in aqueous medium using either the in situ deacetylation of the catalyst or the previously deacetylated catalyst. The catalytic condition using in situ deacetylation was more efficient because it avoids an additional deprotection step.

Graphical abstract: Rational design of galactopyranoside-substituted N-heterocyclic carbene palladium(ii) complexes. Stable and efficient catalyst for C–C coupling in aqueous media

Supplementary files

Article information

Article type
Paper
Submitted
23 נוב 2023
Accepted
20 דצמ 2023
First published
04 ינו 2024
This article is Open Access
Creative Commons BY license

RSC Adv., 2024,14, 1626-1633

Rational design of galactopyranoside-substituted N-heterocyclic carbene palladium(II) complexes. Stable and efficient catalyst for C–C coupling in aqueous media

A. W. Hobsteter, M. J. Lo Fiego and G. F. Silbestri, RSC Adv., 2024, 14, 1626 DOI: 10.1039/D3RA08031E

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