Journal
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Volume -, Issue 32, Pages 5499-5506Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejic.201402744
Keywords
Carbene ligands; Enynes; Cyclization; Gold; Arsenic
Categories
Funding
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-48406-P]
- Junta de Castilla y Leon [GR 169 and VA256U13]
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Neutral gold complexes with hydrogen-bond-supported heterocyclic carbene (HBHC) and nitrogen acyclic carbene (NAC) ligands have been synthesized by the reactions of isocyanogold derivatives [AuCl(CNR)] with amines. Cationic [Au(carbene)(AsPh3)][SbF6] complexes have also been prepared. The catalytic activity of both types of complex (for the former, AgSbF6 is used to extract the halide ligand) in the skeletal rearrangement and methoxycyclization of enynes has been studied. The cationic complexes with AsPh3 are active but slower; advantageously, they do not decompose during the catalysis. In contrast, the catalysts formed in situ from the neutral halide complexes are very fast but undergo decomposition. An interesting trade-off was found by adding substoichiometric amounts of AsPh3 (e.g., 10 mol-%) relative to the gold catalyst {[Au(carbene)Cl] + AgSbF6}, which prevents or dramatically reduces the decomposition. This protecting ligand promises to prevent or minimize the undesired decomposition of gold catalysts.
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