63167-05-5Relevant academic research and scientific papers
Aminoarenethiolato-copper(I) as (pre-)catalyst for the synthesis of diaryl ethers from aryl bromides and sequential C-O/C-S and C-N/C-S cross coupling reactions
Sperotto, Elena,Van Klink, Gerard P.M.,De Vries, Johannes G.,Van Koten, Gerard
experimental part, p. 9009 - 9020 (2011/01/04)
A small library of 2-aminoarenethiolato-copper(I) (CuSAr) complexes was tested as (pre-)catalysts in the arylation reaction of phenols with aryl bromides. These copper(I) (pre-)catalysts are thermally stable, soluble in common organic solvents, and allow reactions of 6 h at 160 °C with low catalyst loadings of 2.5 mol %. Among the (pre-)catalysts screened, 2-[(dimethylamino)methyl]benzenethiolato-copper(I) (1c) led to the best results and provided good to excellent yields of various substituted diaryl ethers. Mechanistic studies showed that at early stages of the C-O coupling reaction the CuSAr complex is converted into CuBr(PhSAr) via selective coupling of the monoanionic arenethiolato ligand with phenyl bromide with formation of CuBr. In addition, the first results are shown involving a multi-component reaction (MCR) protocol for the in situ synthesis of propargylamines and their subsequent conversion involving a C-O cross coupling reaction. Furthermore, two examples of sequential C-O/C-S and C-N/C-S cross coupling reactions have been carried out on the same dihalo-pyridine substrate in a one-pot process with the same (CuSAr) (pre-)catalyst (overall yields 40-80%).
Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols
Sperotto, Elena,Van Klink, Gerard P. M.,De Vries, Johannes G.,Van Koten, Gerard
, p. 5625 - 5628 (2008/12/21)
(Chemical Equation Presented) A protocol for the copper-catalyzed aryl-sulfur bond formation between aryl iodides and thiophenols is reported. The reaction is catalyzed by a low amount (1-2.5 mol %) of readily available and ligand-free copper iodide salt. A variety of diaryl thioethers are synthesized under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.
Synthesis, structure and catalytic activity of thioether-phosphane complexes of Pd(II) and Pt(II)
Dilworth, Jonathan R.,Maresca Von Beckh, W. Carlo A.,Pascu, Sofia I.
, p. 2151 - 2161 (2007/10/03)
New thioether-phosphanes 2-RSC6H4CH 2PPh2 (RS～PPh2: R = Me, 'Bu, Ph) and the corresponding complexes [PdCl2(MeS～PPh2)], [PdCl 2('BuS～PPh2)], [PdCl2/su
POTENTIAL ANTIDEPRESSANTS: 2-(PHENYLTHIO)ARALKYLAMINE
Jilek, Jiri,Urban, Jiri,Taufmann, Petr,Holubek, Jiri,Dlabac, Antonin,et al.
, p. 1995 - 2008 (2007/10/02)
Reactions of 2-(phenylthio)benzyl chloride with dimethylamine, diethylamine, pyrrolidine, piperidine, morpholine, and 1-methylpiperazine afforded the title compounds VI-XI.Reaction of 2-(phenylthio)benzaldehyde with nitromethane gave the nitrostyrene XIV which was reduced with lithium aluminium hydride to 2-(2-phenylthio)phenyl)ethylamine (XVI).This was transformed to the N-methyl and N,N-dimethyl derivatives XVIII and XIX.The Claisen reaction of (2-(2-phenylthio)phenyl)acetonitrile with ethyl acetate afforded the compound XXI which was cleaved by phosphoric acid to (2-(phenylthio)phenyl)acetone (XX).The Leuckart-Wallach reaction afforded the formamide XXIII which was used as starting material for preparing the amines XXIV-XXVI.The alternative approach to these compounds starting by reaction of the aldehyde XII with nitroethane was complicated by the fact that in addition to the nitropropene XV 2-(phenylthio)benzonitrile was also formed.The synthetic use of the inhomogenous XV resulted then in mixtures of amines XXIV-XXVI with IV-VI which was followed by means of mass and 1H NMR spectra.The amines XXIV-XXVI were oxidized to the sulfoxides XXVII-XXIX.The oily bases were transformed to crystalline salts and spectra of all homogeneous bases were recorded.Pharmacological testing showed the amine VI (VUFB-15370) to be a promising potential antidepressant.The amines XI and XXV showed also pharmacological profile of potential antidepressant.
