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

Following a rational design, three novel palladium(ii) complexes bearing galactopyranoside-based -heterocyclic carbene ligands have been synthesized transmetalation of the corresponding Ag(i) complexes. Palladium(ii) complexes have been characterized by NMR, FT-IR and elemental analysis. Catalytic s...

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Bibliographic Details
Published in:RSC advances 2024-01, Vol.14 (3), p.1626-1633
Main Authors: Hobsteter, Ariana W, Lo Fiego, Marcos J, Silbestri, Gustavo F
Format: Article
Language:English
Subjects:
Aqueous solutions
Carbenes
Catalysts
Chemical analysis
Chemical reactions
Chemistry
Cross coupling
NMR
Nuclear magnetic resonance
Palladium
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Summary:Following a rational design, three novel palladium(ii) complexes bearing galactopyranoside-based -heterocyclic carbene ligands have been synthesized 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 deacetylation of the catalyst or the previously deacetylated catalyst. The catalytic condition using deacetylation was more efficient because it avoids an additional deprotection step.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra08031e