NHC-heterocycle carbene gold catalyst intercalated in Layered Double Hydroxides as reusable hybrid catalyst in acidic medium
Source abstract
Abstract
NHC-heterocyclic carbene metal complexes are efficient catalysts used for the oxidation, amination, cycloaddition or hydration of alkynes. Immobilization of such complex is a strategy to avoid its decomposition/deactivation and allow its recycling. One limitation of the immobilization of carbene metal complexes is the acidic pH required to perform the catalysis of hydration of alkynes. The support used must be resistant in such conditions. Layered Double Hydroxides (LDH) is a widely used material as catalyst support due to their tunable chemical composition and flexible open structure. However, the LDH phases usually found as catalyst support in the literature are chemically instable under severe conditions. In particular, when operating in extreme acidic pH. This study describes the development of a pH-resistant support by screening of LDH with various composition and formulation in order to obtain a stable material at pH down to 3.0, conditions required for a model reaction, the hydration of propargyl alcohol. Then, the intercalation of a NHC-heterocyclic carbene gold anionic complex (NHC-Au) was optimized and fully characterized. The newly heterogeneous catalysts were evaluated for the targeted hydration catalysis reaction. The selected support, a LiAl2 phase obtained by urea method and dried at 80 °C, allowed to immobilized up to 75% of the gold complex. The intercalated catalyst was finally used for the hydration of several alkynes with yields between 84% and 100% and was recycled up to 12 cycles without any activity loss.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Catalytic Cross-Coupling Reactions · Nanomaterials for catalytic reactions · Layered Double Hydroxides Synthesis and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (54)
Show source-provided references
1. Nanohybrid layered double hydroxides used to remove several dyes from water10.3390/chemengineering3020041 ↗
2. Thermochemistry and aqueous solubilities of hydrotalcite-like solids10.1126/science.1069797 ↗
3. Eudragit® and hydrotalcite-like anionic clay composite system for diclofenac colonic delivery10.1016/j.micromeso.2008.02.014 ↗
4. Stability of hydrotalcite (Mg-Al layered double hydroxide) in presence of different anions10.1016/j.cemconres.2021.106674 ↗
5. Layered double hydroxide stability. 1. Relative stabilities of layered double hydroxides and their simple counterparts10.1021/cm980523u ↗
6. Review of the synthesis of layered double hydroxides: a thermodynamic approach10.1590/S0100-40422004000400015 ↗
7. Structure of bayerite-based lithium−aluminum layered double hydroxides (LDHs): observation of monoclinic symmetry10.1021/ic9016728 ↗
8. Polytypism in the lithium–aluminum layered double hydroxides: the [LiAl2(OH)6]+ layer as a structural synthon10.1021/ic200312g ↗
9. Highly tunable catalyst supports for single-site ethylene polymerization10.1021/cm503433q ↗
10. LiAl2(OH)6OH.2H2O solubility product and dihydrogen radiolytic production rate under γ-irradiation10.1016/j.jnucmat.2018.05.013 ↗
11. Tunable surface charge and hydrophilicity of sodium polyacrylate intercalated layered double hydroxide for efficient removal of dyes and heavy metal ions10.1016/j.colsurfa.2021.126384 ↗
12. Post-functionalization of metal–NHC complexes: a useful toolbox for bioorganometallic chemistry (and beyond)?10.1016/j.jorganchem.2014.10.012 ↗
13. N-heterocyclic carbene complexes of Au, Pd, and Pt as effective catalysts in organic synthesis10.1007/128_2010_118 ↗
14. Bio-nanocomposites based on layered double hydroxides10.1021/cm0483240 ↗
15. PMO-immobilized AuI-NHC complexes: heterogeneous catalysts for sustainable processes10.1002/cphc.201701102 ↗
16. Solubility and release of fenbufen intercalated in Mg, Al and Mg, Al, Fe layered double hydroxides (LDH): the effect of Eudragit® S 100 covering10.1016/j.jssc.2010.10.017 ↗
17. Structural aspects of layered double hydroxides
18. Synthesis and structural characterization of water-soluble gold(I) N-heterocyclic carbene complexes. An X-ray absorption fine structure spectroscopy (XAFS) study10.1021/om400663a ↗
19. A structure/catalytic activity study of gold(i)–NHC complexes, as well as their recyclability and reusability, in the hydration of alkynes in aqueous medium10.1039/C5CY01278C ↗
20. Sol–Gel immobilized N-heterocyclic carbene gold complex as a recyclable catalyst for the rearrangement of allylic esters and the cycloisomerization of γ-alkynoic acids10.1002/cctc.201600632 ↗
21. Sulfonated N-heterocyclic carbenes for Suzuki coupling in water10.1039/B703658B ↗
22. Chapter 13.1 Layered double hydroxides10.1016/S1572-4352(05)01039-1 ↗
23. Layered double hydroxides (LDH)10.1016/B978-0-08-098258-8.00025-0 ↗
24. Chemical bonding in transition metal carbene complexes10.1016/j.jorganchem.2005.08.054 ↗
25. N-heterocyclic carbene gold(I) and copper(I) complexes in C–H bond activation10.1021/ar200188f ↗
26. Mixing chemo- and biocatalysis for rare monosaccharide production by combining aldolase and N-heterocyclic carbene gold catalysts10.1039/D2GC00667G ↗
27. Unsymmetrical indazolyl-pyridinyl-triazole ligand-promoted highly active iridium complexes supported on hydrotalcite and its catalytic application in water10.1039/C7GC02892J ↗
28. New insights in MgAl and MgFe-LDH affinity towards carbon dioxide – role of the hydrophilic character on CO2 retention strength10.1016/j.clay.2020.105829 ↗
29. Synthesis, characterization, and catalytic activity of anionic iron(III) porphyrins intercalated into layered double hydroxides10.1016/j.jcat.2008.04.026 ↗
30. Water-soluble gold–N-heterocyclic carbene complexes for the catalytic homogeneous acid- and silver-free hydration of hydrophilic alkynes10.1002/adsc.201500729 ↗
31. Suzuki cross-coupling reaction over a palladium–pyridine complex immobilized on hydrotalcite10.1016/j.catcom.2006.05.013 ↗
32. Orthometallation of N-substituents at the NHC ligand of [Rh(Cl)(COD)(NHC)] complexes: its role in the catalytic hydrosilylation of ketones10.1039/C4CY01556H ↗
33. Ab-initio structure determination of LiSbWO6 by X-ray powder diffraction10.1016/0025-5408(88)90019-0 ↗
34. Enteric-coated layered double hydroxides as a controlled release drug delivery system10.1016/j.ijpharm.2004.08.016 ↗
35. Review of gold(I) N-heterocyclic carbenes10.1139/v05-087 ↗
36. N-Heterocyclic carbenes in gold catalysis10.1039/b711132k ↗
37. [(NHC)AuI]-catalyzed acid-free alkyne hydration at part-per-million catalyst loadings10.1021/ja809403e ↗
38. Electrochemical study of anionic ferrocene derivatives intercalated in layered double hydroxides: application to glucose amperometric biosensors10.1002/elan.200804407 ↗
39. The development and catalytic uses of n-heterocyclic carbene gold complexes10.1021/ar1000764 ↗
40. Importance of purity evaluation and the potential of quantitative 1H NMR as a purity assay10.1021/jm500734a ↗
41. Gold(I) NHC catalysts immobilized to amphiphilic block copolymers: a versatile approach to micellar gold catalysis in water10.1002/cctc.202200727 ↗
42. [(NHC)AuCl]-catalyzed Meyer–Schuster rearrangement: scope and limitations10.1016/j.tet.2008.10.111 ↗
43. Recent developments of the program FULLPROF. Commission on powder diffraction (IUCr)
44. Silica-immobilized NHC-gold(I) complexes: versatile catalysts for the functionalization of alkynes under batch and continuous flow conditions10.1021/acscatal.7b02142 ↗
45. Effect of drying on the fabrication of MgAl layered double hydroxides10.1021/acsomega.1c03581 ↗
46. Regulating surface-interface structures of Zn-incorporated LiAl-LDH supported ru catalysts for efficient benzene hydrogenation to produce cyclohexene10.1002/cctc.202200125 ↗
47. Recent progress in N-heterocyclic carbene gold-catalyzed reactions of alkynes involving oxidation/amination/cycloaddition10.3390/catal10030350 ↗
48. Structure of lithium aluminum hydroxide dihydrate (LiAl2(OH)7.2H2O)10.1021/cm00027a011 ↗
49. Rietveld refinement of Debye-Scherrer synchrotron X-ray data from Al2O310.1107/S0021889887087090 ↗
50. (Tetrahydrothiophene)gold(I) or gold(III) Complexes10.1002/9780470132579.ch17 ↗
51. Au-NHC@Porous organic polymers: synthetic control and its catalytic application in alkyne hydration reactions10.1021/cs400983y ↗
52. Electronic effects of support doping on hydrotalcite-supported iridium n-heterocyclic carbene complexes10.1021/acsomega.2c02593 ↗
53. Whittingham · 1982
54. Recent innovative developments of layered double hydroxide-based hybrids and nanocomposite catalysts