Gold(I)-Catalyzed Direct Alkyne Hydroarylation in Ionic Liquids: Mechanistic Insights

The factors determining the catalytic performance of a recently discovered system for direct intermolecular alkyne hydroarylations, comprising a gold(I) complex of general formula LAuX (L = neutral ligand; X = weakly coordinating counteranion) and an ionic liquid as solvent, have been investigated....

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Bibliographic Details
Published in:Catalysts 2023-04, Vol.13 (5), p.822
Main Authors: Bonfante, Sara, Bax, Pietro, Baron, Marco, Biffis, Andrea
Format: Article
Language:English
Subjects:
alkyne
Alkynes
Anions
arene
C-H activation
Catalysis
Catalysts
Chemical reactions
Gold
hydroarylation
Hydrogen
Ionic liquids
Ions
Ligands
Optimization
Poisons
Solvents
Substrates
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Summary:The factors determining the catalytic performance of a recently discovered system for direct intermolecular alkyne hydroarylations, comprising a gold(I) complex of general formula LAuX (L = neutral ligand; X = weakly coordinating counteranion) and an ionic liquid as solvent, have been investigated. In particular, the effect of the ionic liquid anion, cation, and of the electronic and steric properties of the neutral ligand L have been considered. The results of the investigation shed some light in particular on the role of the anion, which is multiform and can potentially influence the catalytic performance in many respects, and on the role of the neutral ligand, which should be a relatively poor electron donor but not so much as to compromise the stability of the catalyst. Knowledge of the factors affecting catalytic performance will speed up the optimization of this catalytic system, in the case of direct alkyne hydroarylations with different substrates, and will also facilitate the extension of its application to other reactions.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal13050822