52089-10-8Relevant academic research and scientific papers
Copper nanopowder catalyzed cross-coupling of diaryl disulfides with aryl iodides in PEG-400
Wu, Xiang-Mei,Yan, Guo-Bing
supporting information, p. 537 - 542 (2015/04/27)
An eco-friendly thiolation via diaryl disulfides and aryl iodides under ligand-free conditions is reported. With copper nanopowder as catalyst and PEG-400 as solvent, a variety of unsymmetrical diaryl sulfides are synthesized in good to excellent yields. The process is free from foul-smelling and unstable thiols and the copper nanopowder-PEG-400 catalytic system can be directly reused for four repetitive cycles.
Transition-metal-free acid-mediated synthesis of aryl sulfides from thiols and thioethers
Wagner, Anna M.,Sanford, Melanie S.
, p. 2263 - 2267 (2014/04/03)
The preparation of diaryl and alkyl aryl sulfides via acid-mediated coupling of thiols and thioethers with diaryliodonium salts is reported. The scope, limitations, and mechanism of the transformation are discussed.
A very active Cu-catalytic system for the synthesis of aryl, heteroaryl, and vinyl sulfides
Kabir, M. Shahjahan,Lorenz, Michael,Van Linn, Michael L.,Namjoshi, Ojas A.,Ara, Shamim,Cook, James M.
experimental part, p. 3626 - 3643 (2010/07/14)
Figure presented cis-1,2-Cyclohexanediol (L3) has been shown to be an efficient and versatile bidentate O-donor ligand that provides a highly active Cu-catalytic system. It was more effective than diols such as trans-1,2-cyclohexanediol or ethylene glycol. This commercially available cis-1,2-cyclohexanediol ligand facilitated the Cu-catalyzed cross-coupling reactions of alkyl, aryl, or heterocyclic thiols with either alkyl, aryl, heterocyclic, or substituted vinyl halides. This new catalytic system promoted the mild and efficient stereo- and regiospecific synthesis of biologically important vinyl sulfides. The yields obtained using electron-rich substituted vinyl sulfides with this catalyst system are generally 75-98%. Most importantly, this singular catalyst system is extremely versatile and provides entry into a wide range of sulfides. This method is particularly noteworthy given its mild reaction conditions, simplicity, generality, and exceptional level of functional group tolerance.
Manganese(II), nickel(II), and palladium(II) complexes of a terpyridine-Like ligand containing a sulfur linkage, and an analogous NCN pincer palladium(II) complex: Synthesis, characterization, and Pd-Catalyzed reactions
Hirotsu, Masakazu,Tsukahara, Yuhei,Kinoshita, Isamu
experimental part, p. 1058 - 1066 (2010/12/18)
Coordination properties of new polypyridines containing a single sulfur linkage, 6-(2″-pyridylthio)-2, 2′-bipyridine (L1) and 1-(2′-pyridyl)-3-(2″-pyridylthio)benzene (HL2), are described. The manganese(II) and nickel(II) complexes of the terpyridine-like ligand L1, [MnCl2(L1)] (1), [NiCl(μ-Cl)(L1)]2 (2), and [Ni(L1)2](SbF6)2 (3), were prepared and characterized by UV-vis spectroscopy and X-ray crystallography. The palladium(II) complex [PdCl(L1)]Cl (4) was synthesized from L1 and Li 2[PdCl1] at room temperature, while the corresponding NCN pincer complex of L2, [PdCl(L2)] (5), was synthesized in DMSO at 150 °C by cyclopalladation of the ligand precursor HL2. The crystal structures of 4 and 5 revealed similar coordination geometries around Pd except for the longer Pd-Cl distance in 5, which is induced by the strong trans influence of the Pd-C bonding. The NMR spectra of 4 showed partial dissociation of L1 in DMSO-d 6, which was not observed for L2 in 5. Catalytic activities of 4 and 5 for the Mizoroki-Heck reaction were investigated, and the lower activity of 5 can be related to the strong σ-donating character of L2.
Simple, efficient and recyclable catalytic system for performing copper-catalyzed C-S coupling of thiols with aryl iodides in PEG and PEG-H2O
She, Jin,Jiang, Zheng,Wang, Yanguang
supporting information; scheme or table, p. 593 - 596 (2009/05/11)
A new protocol for the coupling of aryl iodides with thiophenols or alkanethiols is reported. The reaction is catalyzed by CuI-PEG or CuI-PEG-H2O system in the absence of ligands and volatile organic solvents. A variety of functionalized aryl sulfides are prepared in excellent yields. The isolation of the products is readily performed by the extraction with diethyl ether or petroleum ether, and the CuI-PEG catalyst can be reused without significant loss in activity. The simple catalytic system is economically competitive and environmentally friendly.
Recyclable heterogeneous supported copper-catalyzed coupling of thiols with aryl halides: base-controlled differential arylthiolation of bromoiodobenzenes
Bhadra, Sukalyan,Sreedhar, Bojja,Ranu, Brindaban C.
experimental part, p. 2369 - 2378 (2009/12/28)
Alumina-supported copper sulfate efficiently catalyzes the 5-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic halide. The catalyst is inexpensive, non-air sensitive, environmentally friendly and recyclable.
Design, synthesis, enzyme inhibition, and tumor cell growth inhibition of 2-anilinobenzamide derivatives as SIRT1 inhibitors
Suzuki, Takayoshi,Imai, Keiko,Imai, Erika,Iida, Shinsuke,Ueda, Ryuzo,Tsumoto, Hiroki,Nakagawa, Hidehiko,Miyata, Naoki
experimental part, p. 5900 - 5905 (2009/12/24)
A series of 2-anilinobenzamide derivatives were designed, synthesized and evaluated for their SIRT1-inhibitory activity. Among these, compounds 3 and 5 inhibited SIRT1 activity in enzyme assays and suppressed the growth of Daudi and HCT116 cells.
COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS
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Page 40; 63, (2010/02/06)
One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.
A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols
Kwong, Fuk Yee,Buchwald, Stephen L.
, p. 3517 - 3520 (2007/10/03)
(matrix presented) An efficient copper-catalyzed carbon-sulfur bond formation reaction was developed. This method is particularly noteworthy given its experimental simplicity, high generality, and exceptional level of functional group toleration and the low cost of the catalyst system.
Alkyl- and Arylthiodediazoniations of Dry Arenediazonium o-Benzenedisulfonimides. Efficient and Safe Modifications of the Stadler and Ziegler Reactions to Prepare Alkyl Aryl and Diaryl Sulfides
Barbero, Margherita,Degani, Iacopo,Diulgheroff, Nicola,Dughera, Stefano,Fochi, Rita,Migliaccio, Mara
, p. 5600 - 5608 (2007/10/03)
The reaction between dry arenediazonium o-benzenedisulfonimides 1 and sodium thiolates in anhydrous methanol represents an efficient and safe procedure, of general validity, for the preparation of unfunctionalized or variously functionalized alkyl aryl and diaryl sulfides. As a rule, the reaction temperature was maintained at 0-5°C for the alkylthiodediazoniations and at room temperature (20-25°C) for the arylthiodediazoniations. The sulfide yields are generally high; of the 63 considered examples, 43 gave yields greater than 80% and 13 were between 70% and 80%. Lower yields were obtained only when sterically hindered diazonium salts or thiols were used. A good amount of the o-benzenedisulfonimide (8) was always recovered from the reactions and could be reused to prepare salts 1. The copious experimental data collected in homogeneous conditions have offered several starting points for the study of the mechanism of these reactions.
