C S cross-coupling catalyzed by a series of easily accessible, well defined Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)]

Rodríguez-Cruz, Mario A.; Hernández‐Ortega, Simón; Valdés, Hugo; Rufino‐Felipe, Ernesto; Morales‐Morales, David

doi:10.1016/j.jcat.2020.01.016

Cited by 13 publications

(8 citation statements)

References 74 publications

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“…Imidazolium salts 1h , 1i , 1j , and 1k were synthesized through the procedures described in the literature. [ 50–53 ]…”

Section: Methodsmentioning

confidence: 99%

“…Imidazolium salts 1h, 1i, 1j, and 1k were synthesized through the procedures described in the literature. [50][51][52][53] 1 The hCA isoenzymes were purified by Sepharose-4B-L-tyrosinesulfanilamide affinity techniques. [69] After affinity chromatography, the purity of both isoenzymes was determined by SDS-PAGE according to the previous study.…”

Section: X-ray Crystallographymentioning

confidence: 99%

“…To complete the series of imidazolium salts with phthalimide groups, the salts 1h-k were synthesized again for this study as reported previously. [50][51][52][53]…”

Section: Introductionmentioning

confidence: 99%

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Phthalimide‐tethered imidazolium salts: Synthesis, characterization, enzyme inhibitory properties, and in silico studies

Yiğit

Demir

Celepci

et al. 2022

Archiv der Pharmazie

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A series of new imidazolium salts were prepared in good yield by the reaction between 1-alkylimidazole and a variety of alkyl halides. The structures of the compounds were identified by FT-IR, 1 H NMR, and 13 C NMR spectroscopy, elemental analysis, and mass spectrometry. The crystal structure of 1b was determined by the single-crystal X-ray diffraction method. The phthalimidetethered imidazolium salts exhibited inhibition abilities toward acetylcholinesterase (AChE) and human carbonic anhydrases (hCAs) I and II, with K i values in the range of 24.63 ± 3.45 to 305.51 ± 35.98 nM for AChE, 33.56 ± 3.71 to 218.01 ± 25.21 nM for hCA I and 17.75 ± 0.96 to 308.67 ± 13.73 nM for hCA II. The results showed that the new imidazolium salts can play a key role in the treatment of Alzheimer's disease, epilepsy, glaucoma, and leukemia, which is related to their inhibition abilities of hCA I, hCA II, and AChE. Molecular docking and in silico absorption, distribution, metabolism, excretion and toxicity studies were used to look into how the imidazolium salts interacted with the specific protein targets. To better visualize and understand the binding positions and the influence of the imidazolium salts on hCA I, hCA II, and AChE conformations, each one was subjected to molecular docking simulations.

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“…Imidazolium salts 1h , 1i , 1j , and 1k were synthesized through the procedures described in the literature. [ 50–53 ]…”

Section: Methodsmentioning

confidence: 99%

Section: X-ray Crystallographymentioning

confidence: 99%

See 1 more Smart Citation

Phthalimide‐tethered imidazolium salts: Synthesis, characterization, enzyme inhibitory properties, and in silico studies

Yiğit

Demir

Celepci

et al. 2022

Archiv der Pharmazie

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“…However, in 2010, Nicasio and co‐workers studied the C–S bond‐forming ability of an allyl nickel(II) NHC complex that evidenced products in exceptional yields (96%) in 24 h with a catalyst concentration in the range of 1–5 mol% 64 . In this connection, Valdés and Morales–Morales and co‐workers reported three sterically varied phthalimides substituted half‐sandwich nickel NHC complexes, 54–56 (Figure 4), for catalytic C–S coupling reactions 59 . Reaction of N–(2–bromoethyl)phthalimide with 1–methyl/1–butyl/1–benzylimidazole in toluene at reflux conditions afforded respective bromide salts in high yields.…”

Section: Half–sandwich Nickel Nhc Complexes In C–c Cross‐coupling Rea...mentioning

confidence: 99%

Recent advances in catalytic and electrocatalytic applications of half‐sandwich nickel(0/II) N–heterocyclic carbene complexes

Budagumpi,

Narayana,

Keri

et al. 2023

Applied Organom Chemis

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Diverse structural and catalytic features of half‐sandwich nickel N–heterocyclic carbene (NHC) complexes provide an encouraging platform not only to address the drawbacks of other group X (palladium and platinum) metal NHC catalysts but also to bring about their superior performance. The chemistry of nickel NHC complexes has gained substantial interest from the organometallic community owing to their remarkable stability to air and moisture, easier preparation protocols, and availability of wide scope for structural fine tuning in order to achieve targeted applications. The recent progress in the field of half‐sandwich nickel(0/II) NHC complexes is covered in this review article with a special emphasis on the different synthetic strategies employed, structural characterization including spectral and X‐ray diffraction techniques, and surface morphology of the films of complexes. Both, homogeneous and electrocatalytic applications of half‐sandwich nickel NHC complexes are discussed with respect to their potential in various C–C and C–S bond constructions, targeted C–H bond activations, reductions using silylating agents, electrocatalytic glucose sensing, and electrocatalytic hydrogen evolution reactions. Donor functionalized complexes displayed improved catalytic potential in several C–C and C–S coupling reactions over non–functionalized counterparts. Overall, this assessment, from a comprehensive standpoint, affords evidence that is advantageous in the design of novel NHC ligands to access targeted half‐sandwich nickel(0/II) NHC complexes encompassing potential homogeneous catalytic and electrocatalytic applications.

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“…On the other hand, Morales-Morales contributed to the development of this field. [93] They prepared and evaluated a series of Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)] on CÀ S cross-coupling reactions of thiols and iodo-aryls. The reactions were carried out using 5 mol% at 100 °C in DMF.…”

Section: Nickel Catalystsmentioning

confidence: 99%

C−S Cross‐Coupling Reactions Catalyzed by Well‐Defined Copper and Nickel Complexes

2022

Self Cite

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This review presents well-defined copper and nickel complexes that have been used in the formation of CÀ S bonds. The use of Cu or Ni catalysts represent an advantage in comparison with those based on precious metals such as Pd, by being two of the most abundant metals in the earth's crust and thus cheaper. As can be expected the catalytic activity of the different Cu and Ni complexes is strongly dependent on the nature of the ligands used. Thus, multidentate and strong electron-donating ligands are of common use to design highly active species since such ligands are capable to stabilize species in high oxidation states which are key intermediates in the reaction mechanisms of these processes. This being particular true in the case of copper, where Cu(III) produces unstable and reactive species that require an "extra stabilization" during the reaction mechanism. Hence, the reaction mechanisms using copper and nickel complexes as catalysts are also discussed in this paper, including the role of the different ligands during the catalytic processes. Although there is an increasing number of reports on CÀ S cross coupling reactions, due to the relevance of this transformation, they are often difficult to reproduce and not of general use since the actual catalytic species are not identified. Thus, we hope that this report will help to promote the search and synthesis of new ligands for the design of more active welldefined complexes that can be used as catalysts in a more rational manner in the formation of valuable CÀ S bondcontaining species.

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C S cross-coupling catalyzed by a series of easily accessible, well defined Ni(II) complexes of the type [(NHC)Ni(Cp)(Br)]

Cited by 13 publications

References 74 publications

Phthalimide‐tethered imidazolium salts: Synthesis, characterization, enzyme inhibitory properties, and in silico studies

Phthalimide‐tethered imidazolium salts: Synthesis, characterization, enzyme inhibitory properties, and in silico studies

Recent advances in catalytic and electrocatalytic applications of half‐sandwich nickel(0/II) N–heterocyclic carbene complexes

C−S Cross‐Coupling Reactions Catalyzed by Well‐Defined Copper and Nickel Complexes

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