Nickel–Schiff base complex catalyzed C–S cross-coupling of thiols with organic chlorides

Gogoi, Prasanta; Hazarika, Sukanya; Sarma, Manas Jyoti; Sarma, Kamal; Barman, Pranjit

doi:10.1016/j.tet.2014.08.020

Cited by 59 publications

(21 citation statements)

References 39 publications

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“…Ni(II) Schiff base complexes efficiently catalyze C-S cross-coupling of thiols with organic chlorides [23]. Ni(II) complexes of chelating ligands incorporating thioether and imine donors have relevant properties with various metalloproteins such as blue copper proteins, hemocyanin, tyrosinase and metalloenzymes as well as their stability [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Nickel(II), copper(II), cobalt(II), and palladium(II) complexes with a Schiff base: crystal structure, DFT study and copper complex catalyzed aerobic oxidation of alcohol to aldehyde

Sarma

Devi

Kalita

et al. 2015

Journal of Coordination Chemistry

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Ni(II), Cu(II), Co(II) and Pd(II) complexes were synthesized with a Schiff base containing thioether with ONS-donors chelating to the metal center. The ligand and complexes were characterized by elemental analysis, FT-IR, 1 H-NMR, UV-visible spectroscopy and magnetic studies. The crystal structures of the ligand and its Ni(II) and Pd(II) complexes were determined by single-crystal X-ray diffraction analysis. The structure reveals that ligand-chelated Ni(II) andPd(II) in slightly distorted octahedral and slightly distorted square planar environment, respectively. DFT studies of the Pd(II) complex reveal that the calculated structural parameters are very close with the experimentally observed data. The Cu(II) complex shows very good catalytic activity towards conversion of alcohol to aldehyde under aerobic oxidation with ammonium persulfate.

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Section: Introductionmentioning

confidence: 99%

Nickel(II), copper(II), cobalt(II), and palladium(II) complexes with a Schiff base: crystal structure, DFT study and copper complex catalyzed aerobic oxidation of alcohol to aldehyde

Sarma

Devi

Kalita

et al. 2015

Journal of Coordination Chemistry

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“…3 However, most of the reported methods require a strong base (e.g., t -BuONa), specific or air-sensitive ligands, and high temperature. Such concerns motivate efforts to develop alternative approaches for C–S bond formation.…”

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confidence: 99%

Visible-Light-Promoted C–S Cross-Coupling via Intermolecular Charge Transfer

2017

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Disclosed is a mild, scalable, visible-light-promoted cross-coupling reaction between thiols and aryl halides for the construction of C–S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C–S coupling protocol was applied in drug synthesis and late-stage modifications of active pharmaceutical ingredients. UV–vis spectroscopy and time-dependent density functional theory calculations suggest that visible-light-promoted intermolecular charge transfer within the thiolate–aryl halide electron donor–acceptor complex permits the reactivity in the absence of catalyst.

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“…[20] c Reaction performed at 100°C. water, various solvents such as PEG400, dimethylformamide (DMF) and dimethylsulfoxide (DMSO) in the absence of phase transfer agent were investigated (Table 1, entries [6][7][8][9]. It was observed that in addition to water, DMF is also a suitable solvent for this reaction ( (2 ml) at 60°C were found to be ideal reaction conditions for the synthesis of phenylaryl sulfide.…”

Section: Nife 2 O 4 Mnp-catalysed Synthesis Of Sulfides Through Cromentioning

confidence: 99%

“…[3] Cross-coupling reactions using transition metal catalysts such as Cu, Pd, Fe, Ni, Co and In are powerful tools for the construction of carbon-sulfur bonds. [4][5][6][7][8][9][10] The major drawbacks of these protocols are using volatile, less available, expensive and foul-smelling thiols as substrates that can lead to serious safety and environmental problems. To overcome these drawbacks, various persulfides (thiol surrogates) have been employed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of diaryl sulfides via nickel ferrite‐catalysed C─S bond formation in green media

Farzin

Rahimi

Amiri

et al. 2018

Applied Organom Chemis

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NiFe2O4 magnetic nanoparticles (MNPs) were synthesized, characterized and applied as an air‐stable, inexpensive and magnetically separable nanocatalyst for the synthesis of structurally diverse sulfides. Efficient methodologies were developed for the synthesis of unsymmetric diaryl sulfides via odourless and one‐pot reactions of triphenyltin chloride/S8 or arylboronic acid/S8 as thiolating agents with aryl halides or nitroarenes as starting materials in the presence of base (K2CO3 or NaOH) and NiFe2O4 MNPs as a catalyst in water or poly (ethylene glycol) as solvent at 80–110 °C. Free from ligand and the unpleasant smell of thiols and with the use of magnetically reusable nanocatalyst, green solvents and commercially available and cheap sulfur source and starting materials, these methods are more eco‐friendly and practical than available protocols for the synthesis of sulfides.

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Nickel–Schiff base complex catalyzed C–S cross-coupling of thiols with organic chlorides

Cited by 59 publications

References 39 publications

Nickel(II), copper(II), cobalt(II), and palladium(II) complexes with a Schiff base: crystal structure, DFT study and copper complex catalyzed aerobic oxidation of alcohol to aldehyde

Nickel(II), copper(II), cobalt(II), and palladium(II) complexes with a Schiff base: crystal structure, DFT study and copper complex catalyzed aerobic oxidation of alcohol to aldehyde

Visible-Light-Promoted C–S Cross-Coupling via Intermolecular Charge Transfer

Synthesis of diaryl sulfides via nickel ferrite‐catalysed C─S bond formation in green media

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