- Air-stable binuclear Titanium(IV) salophen perfluorobutanesulfonate with zinc power catalytic system and its application to C–S and C–Se bond formation
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An air-stable μ-oxo-bridged binuclear Lewis acid of titanium(IV) salophen perfluorobutanesulfonate [{Ti(salophen)H2O}2O][OSO2C4F9]2 (1) was successfully synthesized by the reaction of TiIV(salophen)Cl2 with AgOSO2C4F9 and characterized by techniques such as IR, NMR and HRMS. This complex was stable open to air over a year, and exhibited good thermal stability and high solubility in polar organic solvents. The complex also had relatively strong acidity with a strength of 0.8 Ho ≤ 3.3, and showed high catalytic efficiency towards various C–S and C–Se bond formations in the presence of zinc power. This catalytic system affords a mild and efficient approach to synthesis of thio- and selenoesters, α-arylthio- and seleno-carbonyl compounds, and thio- and selenoethers.
- Wang, Lingxiao,Qiao, Jie,Wei, Jiancong,Liang, Zhiwu,Xu, Xinhua,Li, Ningbo
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- Synthesis of α-arylthioacetones using TEMPO as the: C 3 synthon via a reaction cascade of sequential oxidation, skeletal rearrangement and C-S bond formation
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Here, we present an unprecedented pathway to α-sulfenylated carbonyl compounds from commercially available thiols and universally employed TEMPO and its analogues, which act as C3 synthons through skeletal rearrangement under simple and metal-f
- Zou, Jiao-Xia,Jiang, Yi,Lei, Shuai,Yin, Gao-Feng,Hu, Xiao-Ling,Zhao, Quan-Yi,Wang, Zhen
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supporting information
p. 2341 - 2345
(2019/03/07)
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- Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Crystal structure, DFT study and catalytic investigation of palladium and nickel complexes towards deacylative sulfenylation of active methylenes and regioselective 3-sulfenylation of indoles: Via thiouronium salt formation
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A series of Ni(ii), Cu(ii), Co(ii), and Pd(ii) complexes have been synthesized with a chelating Schiff base ligand coordinated to a metal center with ONS donor atoms. The ligand and complexes are characterized by elemental analysis and spectroscopic techniques like FT-IR, 1H-NMR, and UV-Visible spectroscopy. The single crystal structure of the Pd(ii) complex is obtained by X-ray diffraction analysis and exhibits slightly distorted square planar geometry. The structure is optimized by DFT, TD-DFT calculation to elaborate the electronic structure and NBO for the charge distribution analysis of the Pd(ii) complex. The synthesized Pd(ii) and Ni(ii) complexes as catalysts have been investigated in the C-S cross-coupling of indoles and active methylenes. The metal propelled regioselective transformation afforded 3-sulfenylated indoles while β-diketones favored deacylated monosulfenyl ketones in an excellent yield via thiouronium salt formation. The Pd(ii) complex displays slightly better reactivity whereas the Ni(ii) complex is cost-efficient. The method is fast, easy to handle and cost effective in terms of high reactivity of catalysts, use of non-toxic solvents, and cheaper aryl halides and thiourea replace conventional sulfur sources, providing a practical access to organic transformations.
- Devi, Namita,Sarma, Kuladip,Rahaman, Rajjakfur,Barman, Pranjit
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p. 4583 - 4595
(2018/04/03)
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- Cs2CO3-promoted carbon–sulfur bond construction via cross dehydrogenative coupling of thiophenols with acetonitrile
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A novel protocol for the construction of carbon–sulfur bonds has been achieved via halogen-free Cs2CO3-promoted cross dehydrogenative coupling (CDC) of thiophenols with acetonitrile. This transformation provides a straightforward route to the synthesis of sulfenylated acetonitriles in up to 80% yield.
- Chen, Qian,Huang, Yulin,Wang, Xiaofeng,Wen, Chunxiao,Yan, Xinxing,Zeng, Jiekun
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supporting information
p. 3928 - 3931
(2017/09/21)
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- An Unexpected Domino Reaction of β-Keto Sulfones with Acetylene Ketones Promoted by Base: Facile Synthesis of 3(2H)-Furanones and Sulfonylbenzenes
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An unexpected domino reaction of β-keto sulfones with acetylene ketones has been developed. The domino reaction of β-keto sulfones with diynones proceeded smoothly in the presence of 30 mol% K2CO3 without other additives, and afforded the novel 3(2H)-furanone derivatives. On replacing the diynones with terminal alkyne ketones, the reaction regioselectivity was changed and sulfonylbenzenes were obtained via benzannulation in good yields. (Figure presented.).
- Tong, Wei,Li, Qian-Yu,Xu, Yan-Li,Wang, Heng-Shan,Chen, Yan-Yan,Pan, Ying-Ming
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supporting information
p. 4025 - 4035
(2017/11/21)
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- A sulfur-containing amino acid amide carbamate derivative and application thereof
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The invention belongs to the field of plant fungicides, and relates to sulfur-containing amino acid amide carbamate derivatives of which the general formulas I are shown in the description and pharmaceutically acceptable salts of the sulfur-containing amino acid amide carbamate derivatives. In the general formulas I, substituent groups R1, R2 and n are defined in the description. The invention further relates to preparation methods of compounds related to the general formulas I, special intermediates developed for the preparation of the compounds, and application of the compounds to prevention and control of plant diseases.
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Paragraph 0033-0034
(2017/08/09)
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- Fe-Mediated S-S Bond Cleavage and Its Application in the Synthesis of α-Arylthio Carbonyl Compounds
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In the presence of iron dust, diaryl disulfides react with α-bromo carbonyl compounds to obtain α-arylthio carbonyl compounds in good yield at 90 °C under an N2 atmosphere, using commercial dimethylformamide (DMF) as solvent. The possible reaction mechanism is that the disulfide is reduced by iron dust to give ArSFeSAr and then reacted with α-bromo carbonyl compounds to give product α-arylthio carbonyl compounds and FeBr2.
- He, Yun-Hua,Li, Ning-Bo,Chen, Jin-Yang,Qiu, Ren-Hua,Wang, Xie,Xu, Xin-Hua
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p. 1817 - 1822
(2015/08/06)
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- α-Arylchalcogenation of acetone with diaryl dichalcogenide via metal-free oxidative C(sp3)-H bond functionalization
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Direct α-arylchalcogenation of acetone with diaryl dichalcogenides has been achieved by using a mixture of TBHP and DTBP oxidants at 120 °C without transition-metal catalyst via oxidative C(sp3)-H bond functionalization. The method exhibits good functional group tolerance and products were isolated in moderate to high yields.
- Yan, Guobing,Borah, Arun Jyoti,Wang, Lianggui,Pan, Zhangjin,Chen, Shuangshuang,Shen, Xuqian,Wu, Xiangmei
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supporting information
p. 4305 - 4307
(2015/06/22)
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- Hydroxysulfenylation of electron-deficient alkenes through an aerobic copper catalysis
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A copper-catalyzed hydroxysulfenylation of α,β-unsaturated esters/amides is reported. The method presents a selective and efficient synthesis of β-hydroxysulfides bearing electron-withdrawing groups. The synthetic utility of this method is demonstrated by the concise synthesis of the anticancer drug bicalutamide.
- Xi, Hui,Deng, Bicheng,Zong, Zhenzhen,Lu, Shenglin,Li, Zhiping
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supporting information
p. 1180 - 1183
(2015/03/14)
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- Copper-Catalyzed Synthesis of α-Thioaryl Carbonyl Compounds Through S-S and C-C Bond Cleavage
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A method to access α-thioaryl ketones and α-thioaryl esters employing copper acetate (hydrate) as catalyst and readily accessible diaryl disulfides and β-diketones (or β-keto esters) has been developed. Both alkyl- and aryl-substituted carbonyl compounds can be prepared. Copyright
- Zou, Liang-Hua,Priebbenow, Daniel L.,Wang, Long,Mottweiler, Jakob,Bolm, Carsten
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supporting information
p. 2558 - 2563
(2013/10/21)
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- NEW COMPOUNDS
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A compound of formula (I), wherein A is S, O or a double bond, and L is a substituted thiazolyl, phenyl or pyridyl. The compound is useful for the treatment of inflammation and cancer.
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Page/Page column 51
(2012/04/04)
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- Preparation and pharmacological evaluation of a novel series of 2-(phenylthio)benzo[b]thiophenes as selective MT2 receptor ligands
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A series of N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)acylamides was synthesized and evaluated for binding affinity and intrinsic activity at melatonin receptors. The affinity of each compound for the melatonin receptors was determined by binding studies on cloned human MT 1 and MT2 receptors expressed in CHO cells. Agonist and antagonist potency was measured on the [35S]GTPγS binding assay for the most interesting compounds. The new derivatives 8-14 showed modest to high selectivity (between 4 and 220) for MT2 receptors. The most selective compound, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)but-3-enamide (14), an MT2 ligand with affinity for the MT 2 receptor similar to that of melatonin and a 220-fold preference over MT1 receptors, acts as a partial agonist. In addition, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl)ethyl)propionamide (9), a nanomolar MT2 ligand with a good selectivity ratio (MT 1/MT2 = 51) shows antagonist activity on both melatonin receptors.
- Mésangeau, Christophe,Fraise, Mika?l,Delagrange, Philippe,Caignard, Daniel Henri,Boutin, Jean Albert,Berthelot, Pascal,Yous, Sa?d
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scheme or table
p. 1835 - 1840
(2011/05/06)
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- Enzyme-catalyzed transfer of a ketone group from an S-adenosylmethionine analogue: A tool for the functional analysis of methyltransferases
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"Chemical equation presented" S-Adenosylmethionine (AdoMet or SAM)-dependent methyltransferases belong to a large and diverse family of group-transfer enzymes that perform vital biological functions on a host of substrates. Despite the progress in genomics, structural proteomics, and computational biology, functional annotation of methyltransferases remains a challenge. Herein, we report the synthesis and activity of a new AdoMet analogue functionalized with a ketone group. Using catechol O-methyltransferase (COMT, EC 2.1.1.6) and thiopurine S-methyltransferase (TPMT, EC 2.1.1.67) as model enzymes, this robust and readily accessible analogue displays kinetic parameters that are comparable to AdoMet and exhibits multiple turnovers with enzyme. More importantly, this AdoMet surrogate displays the same substrate specificity as the natural methyl donor. Incorporation of the ketone group allows for subsequent modification via bio-orthogonal labeling strategies and sensitive detection of the tagged ketone prod cts. Hence, this AdoMet analogue expands the toolbox available to interrogate the biochemical functions of methyltransferases.
- Lee, Bobby W. K.,Sun, He G.,Zang, Tianzhu,Ju-Kim, Byung,Alfaro, Joshua F.,Zhou, Zhaohui Sunny
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supporting information; experimental part
p. 3642 - 3643
(2010/05/15)
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- Reactions of p-toluenesulfenyl chloride with enol acetates. The synthetic potential of the resulting adducts
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Reactions of vinyl and propen-2-yl acetates with p-toluenesulfenyl chloride afforded the corresponding α-chloro-β-(p-tolyl)thioalkyl acetates in nearly quantitative yields.These adducts reacted with some C-nucleophiles in the presence of Lewis acids to gi
- Smit,Yagodkin,Zatonsky
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p. 743 - 747
(2007/10/03)
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- Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: Versatile synthons for enantiopure β-hydroxy sulfoxides
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Humicola lanuginosa lipase-catalyzed acylation of β-hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give β-hydroxy sulfoxides in >99% e.e. The effect of substituents on enantioselectivity is discussed.
- Singh, Satwinder,Kumar, Subodh,Chimni, Swapandeep Singh
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p. 2457 - 2462
(2007/10/03)
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- Chemoselective deoxygenation of sulfoxides with titanium tetraiodide
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Chemoselective deoxygenation of sulfoxides was carried out using TiI4 as a reducing agent to give sulfides in good to excellent yields.
- Shimizu,Shibuya,Hayakawa
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p. 1437 - 1438
(2007/10/03)
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- Synthesis and anticancer activity of new phenyl-ring substituted 4-morpholino-1-phenylthio-2-butanones [Mannich bases]
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The preparation of phenyl-ring substituted 4-morpholino-1-phenylthio-2-butanones 4a-e is described. These compounds were evaluated against P-388 leukemia and human cancer rhinopharynx KB cells in vitro; some compounds were found to exhibit activity agains
- Siatra-Papastaikoudi,Tsotinis,Chinou,Roussakis
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p. 221 - 223
(2007/10/02)
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- CONFORMATIONAL AND ELECTRONIC INTERACTION STUDIES OF α-SUBSTITUTED CARBONYL COMPOUNDS. VI. p-SUBSTITUTED α-PHENYLTHIOACETONES.
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The analysis of the νCO bands in the I.R. spectrum of p-substituted α-phenylthioacetones indicates a cis/gauche rotational isomerism.The slight solvent effect on the αc αg ratios on going from a non polar solvent to a polar one , for the title compounds, as well as the minute sensitivity of the νCO (cis) frequencies on going from electron-attracting to electron-donating substituents are interpreted on the grounds of the Field (F) and Inductive effects, which act in opposition in the cis rotamer, practically cancelling each other.The decreasing cis/gauche population ratio on going from electron-attracting to electron-donating substituents suggests the occurance of the hyperconjugative interaction in the gauche rotamers of the title compounds.The progressive shielding effect on the methylene and carbonyl carbon atoms in the 13C NMR spectra, on going from electron-donating to electron-attracting substituents is ascribed at least in part, to the "Reverse Polar Effect".Keywords: Conformational studies; electronic interaction; Reverse Polar Effect; I.R. spectroscopy; 13C NMR spectroscopy; p-substituted α-phenylthioacetones.
- Olivato, Paulo R.,Guerrero, Sandra A.,Martins, Elizabeth A. L.
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