30519-03-0Relevant articles and documents
Mono- And Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C-S Cross-Coupling
Talukder, Md Muktadir,Miller, Justin T.,Cue, John Michael O.,Udamulle, Chinthaka M.,Bhadran, Abhi,Biewer, Michael C.,Stefan, Mihaela C.
, p. 83 - 94 (2021/01/14)
The usefulness of transition metal catalytic systems in C-S cross-coupling reactions is significantly reduced by air and moisture sensitivity, as well as harsh reaction conditions. Herein, we report four highly air- and moisture-stable well-defined mononuclear and bridged dinuclear α-diimine Ni(II) and Pd(II) complexes for C-S cross-coupling. Various ligand frameworks, including acenaphthene- and iminopyridine-based ligands, were employed, and the resulting steric properties of the catalysts were evaluated and correlated with reaction outcomes. Under aerobic conditions and low temperatures, both Ni and Pd systems exhibited broader substrate scope and functional group tolerance than previously reported catalysts. Over 40 compounds were synthesized from thiols containing alkyl, benzyl, and heteroaryl groups. Also, pharmaceutically active heteroaryl moieties are incorporated from thiol and halide sources. Notably, the bridged dinuclear five-coordinate Ni complex has outperformed the remaining three mono four- or six-coordinate complexes by giving almost quantitative yields across a broad substrate scope.
Method for synthesizing (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate
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Paragraph 0023; 0026; 0027; 0028, (2016/10/31)
The invention relates to a method for synthesizing (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate. The method includes the following steps that in a solvent, 4-mercaptophenol or benzyl chloride or benzyl bromide serves as a raw material, and 4-(benzylthio) phenol is prepared under the action of triethylamine or potassium carbonate or sodium carbonate; in a toluene or cyclohexane or chloroform or dichloroethane solution, 4-(benzylthio) phenol and dimethyl sulfate or potassium iodide are methylated to obtain (4-hydroxyphenyl) methyl benzyl sulfonium sulfate or (4-hydroxyphenyl) methyl benzyl sulfonium iodate; in a methanol or alcohol or isopropanol solution, (4-hydroxyphenyl) methyl benzyl sulfonium sulfate and sodium hexafluoroantimonate are subjected to ion exchange to obtain the target product (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate. The method has the advantages that the raw materials are easy to obtain, the technology is simple, the prepared 4-(benzylthio) phenol is high in purity and does not need to be refined, and the requirement for large-scale industrial production of (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate can be met.
A highly efficient Cu-catalyzed S-transfer reaction: From amine to sulfide
Li, Yiming,Pu, Jiahua,Jiang, Xuefeng
supporting information, p. 2692 - 2695 (2014/06/09)
A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.
