Allylic alkylation and amination using mixed (NHC)(phosphine) palladium complexes under biphasic conditions

Flahaut, Alexandre; Roland, Sylvain; Mangeney, Pierre

doi:10.1016/j.jorganchem.2007.10.012

Cited by 41 publications

(28 citation statements)

References 50 publications

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“…This reaction is usually considered fast and quantitative, so we believe that the effect of the different halides on the catalytic efficiency of the studied complexes is negligible. Furthermore, the reaction forming the active species is influenced by two factors: (i) the strength of the Au-X bond [38], and (ii) the solubility of the silver halide product, [39] both of which decrease along the halogen group. Thus, the removal of the iodide should be more favored than the removal of a bromide or a chloride.…”

Section: Comparison Of the Catalytic Performances Of Au 2 Br 2 L 4 Wimentioning

confidence: 99%

Hydroalkoxylation of Terminal and Internal Alkynes Catalyzed by Dinuclear Gold(I) Complexes with Bridging Di(N-Heterocyclic Carbene) Ligands

et al. 2019

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A series of six dinuclear gold(I) complexes with bridging bidentate N-heterocycic carbene ligands (NHCs) of general formula Au2Br2LX (L = diNHC, X = 1–6) have been studied as catalysts in the intermolecular hydroalkoxylation of terminal and internal alkynes. The best catalytic results have been obtained by using Au2Br2L4, characterized by 2,6-diisopropylphenyl wingtip substituents and a methylene bridging group between the two NHC donors. Complex Au2Br2L4 has been structurally characterized for the first time in this work, showing the presence of intramolecular aurophiclic interaction in the solid state. In the adopted reaction conditions Au2Br2L4 is able to convert challenging substrates such as diphenylacetylene. Comparative catalytic tests by using the mononuclear gold(I) complexes AuIL7 and IPrAuCl have been performed in order to determine the possible presence of cooperative effects in the catalytic process.

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Section: Comparison Of the Catalytic Performances Of Au 2 Br 2 L 4 Wimentioning

confidence: 99%

Hydroalkoxylation of Terminal and Internal Alkynes Catalyzed by Dinuclear Gold(I) Complexes with Bridging Di(N-Heterocyclic Carbene) Ligands

et al. 2019

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“…First, 2‐[2‐(1 H ‐imidazol‐1‐yl)ethyl]‐3‐chloro‐5‐(trifluoromethyl)pyridine ( 2 ) was obtained from the amine derivative 1 . Using different protocols under mild conditions, the Me, benzyl, and 2,3,4,5‐tetra‐ O ‐acetyl‐ d ‐galactocopyranosyl groups were inserted as second substituents .…”

Section: Resultsmentioning

confidence: 99%

Trifluoromethylpyridine-SubstitutedN-Heterocyclic Carbenes Related to Natural Products: Synthesis, Structure, and Potential Antitumor Activity of some Corresponding Gold(I), Rhodium(I), and Iridium(I) Complexes

Maftei¹,

Maftei²,

Jones³

et al. 2016

Helv. Chim. Acta

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This work presents the synthesis, characterization, and application of several new metal(I) complexes with trifluoromethylpyridine-containing N-heterocyclic carbene (NHC) ligands. The metal of choice was gold(I) for compounds 7 -10, rhodium(I) for 11 -12, and iridium(I) for 13 -14, respectively. The trifluoromethylpyridine moiety was incorporated, along with other biologically active moieties, with the intention of modifying the lipophilicity of the complexes, so that the transport of the active units (M-NHC) through the cell wall barrier is facilitated. The biological activity of the complexes was investigated. In vitro assessment of antitumor activity in a panel of 12 human tumor cell lines by a monolayer assay revealed good potency (mean IC 50 12.6 lM) and tumor selectivity for one compound. The solid-state structures of two solvates of compound 7, one with MeOH and one with THF, were determined by X-ray diffraction analysis.

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“…As mentioned above, Roland et al 92 ascribed the dismal selectivity for the phosphine-NHC system to the similarity in the trans effect caused by the phoshine and NHC that is present in the system. As illustrated in Although complex (±)-79 in method C gave dismal yield in the model study, method C was the only method available presently to test out the selectivity of complex (S)-58 that has the bulkiest Ph group.…”

Section: Model Study With Racemic Palladacycle (±)-56mentioning

confidence: 99%

Synthesis, characterization and catalytic application of novel cyclopalladated pyridine functionalized N-heterocyclic carbene complexes

Chiang¹

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Allylic alkylation and amination using mixed (NHC)(phosphine) palladium complexes under biphasic conditions

Cited by 41 publications

References 50 publications

Hydroalkoxylation of Terminal and Internal Alkynes Catalyzed by Dinuclear Gold(I) Complexes with Bridging Di(N-Heterocyclic Carbene) Ligands

Hydroalkoxylation of Terminal and Internal Alkynes Catalyzed by Dinuclear Gold(I) Complexes with Bridging Di(N-Heterocyclic Carbene) Ligands

Trifluoromethylpyridine-SubstitutedN-Heterocyclic Carbenes Related to Natural Products: Synthesis, Structure, and Potential Antitumor Activity of some Corresponding Gold(I), Rhodium(I), and Iridium(I) Complexes

Synthesis, characterization and catalytic application of novel cyclopalladated pyridine functionalized N-heterocyclic carbene complexes

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