- Unusual Deoxidative Coupling Reaction of β-Sulfinyl Esters with Benzylic Trimethylammonium Salts
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A KOH-promoted unusual deoxidative coupling reaction of β-sulfinyl esters with benzylic trimethylammonium salts to produce thioethers is discovered for the first time. If quaternary ammonium salts synthesized from enantiomerically enriched amines are adopted, highly enantiomerically enriched benzyl thioethers (>95-99% ee) with configurations opposite to those of the enantiomerically enriched amines are obtained.
- Chen, Feng,Feng, Hang,He, Ze,Zeng, Qingle,Zhang, Qiaoling
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p. 7806 - 7812
(2021/06/25)
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- Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation
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A nickel-catalyzed oxidative dehydrogenative coupling reaction of alkane with thiol for the construction of C(sp3)-S bond has been established, affording more than 50 alkyl thioethers. Notably, pharmaceutical and agrochemicals, such as Provigil, Chlorbenside and Pyridaben, were readily synthesized by this approach. The sterically hindered ligand BC and disulfide which was formed in situ oxidation of thiol, efficiently avoiding nickel-catalyst poisoning. A set of mechanistic experiments disclose both Ni-catalyzed and Ni-free HAA processes.
- Liu, Shengping,Jin, Shengnan,Wang, Hao,Qi, Zaojuan,Hu, Xiaoxue,Qian, Bo,Huang, Hanmin
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supporting information
(2021/03/15)
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- Preparation method of alkyl sulfide
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The invention relates to a preparation method of alkyl sulfide. The method comprises the following steps: under the protection of nitrogen, sequentially adding transition metal, a nitrogen ligand, a cocatalyst, an oxidant, a solvent, alkane and thiophenol or mercaptan into a reaction tube, carrying out oxidative dehydrogenation coupling reaction at 80-150 DEG C, ending the reaction after 6-48 hours, evaporating the solvent to dryness, and carrying out column chromatography separation to obtain the alkyl sulfide compound. The method is simple in synthesis process, mild in reaction condition, high in yield and easy to industrialize.
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Paragraph 0050
(2019/12/02)
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- Synthesizing method of 2-pyridine methyl sulfide and synthesizing process of related drugs
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The invention relates to a simple synthesizing method of 2-pyridine methyl sulfide and related drugs. The method is characterized in that 2-methyl pyridine n-oxide is used as the raw material and pyridine n-oxide or dichloromethane is used as the solvent to have reaction with trifluoroacetic anhydride to obtain a trifluoroacetate intermediate, purification is not needed, the trifluoroacetate intermediate is allowed to have reaction with thiophenol under the catalysis of lithium bromide or tetrabutyl ammonium bromide and by using toluene or ethyl acetate as the solvent to generate the 2-pyridine methyl sulfide. The method is simple to operate, cheap in reagents, easy in reagent obtaining, mild in reaction conditions, wide in substrate applicability, good in position selectivity, high in yield and the like. In addition, the method is successfully applied to the synthesizing of omeprazole sulfide and rabeprazole sulfide, and the synthesizing method does not need catalysts.
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- Metal- and base-free regioselective thiolation of the methyl C(sp3)-H bond in 2-picoline: N -oxides
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A one-pot, two-step synthesis of pyridine-2-ylmethyl thioethers is developed through a TFAA-mediated [3,3]-sigmatropic rearrangement of pyridine N-oxides and TBAB-catalyzed direct conversion of trifluoroacetates into thioethers under metal- and base-free conditions. This methodology enables thiolation of the unactivated methyl C(sp3)-H bond in 2-picolines with thiols. Remarkable features of the method include high regioselectivity, step- and atom-economy, mild conditions, simple operation, wide substrate scope and scalability. Furthermore, the method has been successfully applied to the synthesis of omeprazole sulfide and rabeprazole sulfide without the need for TBAB catalysis. A comprehensive green chemistry metrics analysis indicated that this method is much more efficient and greener than the reported synthesis of rabeprazole sulfide.
- Wang, Dong,Liu, Zhenlin,Wang, Zhentao,Ma, Xinyue,Yu, Peng
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supporting information
p. 157 - 163
(2019/01/11)
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- Enforcing geometrical constraints on metal complexes using biphenyl-based ligands: Spontaneous reduction of copper(II) by sulfur-containing ligands
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Two biphenyl-based N2S2 ligands, 2,2′-bis-(4-methylimidazol-5-yl)methylsulfanyl)biphenyl (N2S2-mim) and 2,2′-bis(2-pyridylmethylsulfanyl)biphenyl (N2S2-mpy), have been synthesized and their
- Malachowski, Mitchell R.,Adams, Mark,Elia, Nadia,Rheingold, Arnold L.,Kelly, Richard S.
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p. 2177 - 2182
(2007/10/03)
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- Synthesis of new optically active sulfoxides with chelating properties
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Access to enantiomerically pure 2-pyridinylmethyl sulfoxides and β-imino sulfoxides was sought.The latter were obtained in tautomeric mixtures with their enamines by condensation of optically active β-keto sulfoxides with primary amines. 2-Pyridinylmethyl
- Baldenius, Kai-U.,Kagan, Henri B.
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p. 597 - 610
(2007/10/02)
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- Studies on the stereoselective methylation of α-sulfinyl carbanions generated from three isomeric pyridylmethyl π-tolyl sulfoxides and benzyl 2-pyridyl sulfoxide
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A high stereoselectivity in the methylation of 2-pyridylmethyl p-totyl sulfoxide (2a) with lithium diisopropylamide and iodomethane was observed at low temperature. The chelation of Li+ by both the nitrogen atom in the pyridine ring and the sulfinyl oxygen atom in 2a promotes the stereoselectivity as compared with isomeric sulfoxides.
- Furukawa,Hosono,Fujihara,Ogawa
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p. 461 - 465
(2007/10/02)
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- 2-pyridine Derivatives: New Antiinflammatory Agents
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2-pyridine derivatives (1a-e) inhibited the dermal reverse passive Arthus reaction (RPAR) in the rat.In the same model, indomethacin was inactive, and hydrocortisone was active.Compounds 1a-d also significantly reduced exudate volume and white blood cell accumulation in the pleural RPAR.This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin.
- Haviv, Fortuna,DeNet, Robert W.,Michaels, Raymond J.,Ratajczyk, James D.,Carter, George W.,Young, Patrick R.
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p. 218 - 222
(2007/10/02)
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