- Synthesis of Aryl Methyl Sulfides from Arysulfonyl Chlorides with Dimethyl Carbonate as the Solvent and C1 Source
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A new procedure for the synthesis of aryl methyl sulfides from dimethyl carbonate (DMC) and arylsulfonyl chlorides has been achieved. In this strategy, DMC plays a dual role as both, C1 building block and green solvent. Arylsulfonyl chlorides served as the sulfur precursors, and a variety of aryl methyl sulfides were obtained in moderate to excellent yields with good functional group tolerance. Additionally, alkylsulfonyl chloride and dibenzyl carbonate are proven to be suitable substrates as well.
- Miao, Ren-Guan,Qi, Xinxin,Wu, Xiao-Feng
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supporting information
p. 5219 - 5221
(2021/10/19)
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- Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water
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An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.
- Wang, Ying-Yu,Wu, Xiang-Mei,Yang, Ming-Hua
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supporting information
(2020/07/20)
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- Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand
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A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.
- Kuninobu, Yoichiro,Naito, Morio,Torigoe, Takeru,Yamanaka, Masahiro,Zeng, Jialin
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supporting information
(2020/05/08)
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- Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides
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We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.
- Zhang, Bo,Fan, Zhengning,Guo, Zhiqiang,Xi, Chanjuan
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p. 8661 - 8667
(2019/07/03)
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- Chemoenzymatic Deracemization of Chiral Sulfoxides
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The highly enantioselective enzyme methionine sulfoxide reductase A was combined with an oxaziridine-type oxidant in a biphasic setup for the deracemization of chiral sulfoxides. Remarkably, high ee values were observed with a wide range of substrates, thus providing a practical route for the synthesis of enantiomerically pure sulfoxides.
- Nosek, Vladimír,Mí?ek, Ji?í
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supporting information
p. 9849 - 9852
(2018/07/31)
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- IMIDAZOPYRIMIDINE COMPOUNDS USEFUL FOR THE TREATMENT OF CANCER
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A compound of Formula (IA), or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating a PRC2-mediated disease or disorder: wherein A, R3, R4, R6, and R7 are as defined herein.
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Paragraph 00225
(2018/04/12)
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- Metal-Free, DTBP-Mediated Methylthiolation of Arylboronic Acids with Dimethyldisulfide
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An efficient method for the C-S bond formation via the coupling reaction of arylboronic acids with dimethyldisulfide has been developed under the metal-free conditions. This novel protocol provides an attractive route for the synthesis of aryl methyl sulf
- Wu, Xiang-Mei,Lou, Jia-Ming,Yan, Guo-Bing
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supporting information
p. 2269 - 2273
(2016/10/30)
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- Rhodium-Catalyzed ipso-Borylation of Alkylthioarenes via C-S Bond Cleavage
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Rhodium-catalyzed transformation of alkyl aryl sulfides into arylboronic acid pinacol esters via C-S bond cleavage is reported. In combination with transition-metal-catalyzed sulfanyl group-guided regioselective C-H borylation reactions of alkylthioarenes, this method allows the synthesis of a diverse range of multisubstituted arenes.
- Uetake, Yuta,Niwa, Takashi,Hosoya, Takamitsu
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supporting information
p. 2758 - 2761
(2016/06/15)
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- Palladium-Catalyzed ipso-Borylation of Aryl Sulfides with Diborons
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A catalytic Miyaura-type ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C-S bonds into C-B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation was observed in the reaction of diphenyl sulfide.
- Bhanuchandra,Baralle, Alexandre,Otsuka, Shinya,Nogi, Keisuke,Yorimitsu, Hideki,Osuka, Atsuhiro
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supporting information
p. 2966 - 2969
(2016/07/06)
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- TRIAZOLOPYRIMIDINE COMPOUNDS AND USES THEREOF
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A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is provided that has been shown to be useful for treating a PRC2-mediated disease or disorder: wherein R1, R2, R3, R4, R5, and n are as defined herein.
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-
Paragraph 0440; 0441
(2016/07/27)
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- N-Imidazolylation of Sulfoximines from N-Cyano Sulfoximines, 1-Alkynes, and N-Sulfonyl Azides
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The rhodium-catalyzed N-imidazolylation of N-sulfonyl-1,2,3-triazoles with a variety of N-cyano sulfoximines has been developed for the synthesis of N-imidazolyl sulfoximines via elimination of molecular nitrogen. Copper-catalyzed [3+2] cycloaddition followed by rhodium-catalyzed N-imidazolylation from 1-alkynes, N-sulfonyl azides, and N-cyano sulfoximines is also demonstrated for the synthesis of N-imidazolyl sulfoximines in a one-pot procedure.
- Kim, Sanghyuck,Kim, Ji Eun,Lee, Jinsub,Lee, Phil Ho
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supporting information
p. 3707 - 3717
(2016/01/25)
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- Sulfoxide-to-sulfilimine conversions: Use of modified Burgess-type reagents
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Sulfoxides can directly be converted into N-cyanosulfilimines using a new Burgess-type reagent. By applying this strategy with a related reagent variant, synthetically valuable NH-sulfoximines have been prepared from sulfoxides via N-protected sulfilimines. The practical three-step reaction sequence is generally high yielding and applicable to a wide range of substrates. The sulfoxide-to-sulfilimine conversion can also be performed under solvent-reduced conditions in a ball mill. Copyright
- Hendriks, Christine M. M.,Lamers, Philip,Engel, Julien,Bolm, Carsten
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supporting information
p. 3363 - 3368
(2013/12/04)
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- Enantioselective nitrene transfer to sulfides catalyzed by a chiral iron complex
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Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated. Copyright
- Wang, Jun,Frings, Marcus,Bolm, Carsten
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supporting information
p. 8661 - 8665
(2013/09/12)
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- Copper-mediated methylthiolation of aryl halides with DMSO
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A copper-mediated methylthiolation of aryl halides with the widely available DMSO is described. The procedure tolerates a series of functional groups such as methoxy, nitro, chloro, fluoro, trifluoromethyl, formyl and methoxycarbonyl groups. Thus, it represents a simple and facile methylthiolation procedure.
- Luo, Fang,Pan, Changduo,Li, Liping,Chen, Fan,Cheng, Jiang
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supporting information; experimental part
p. 5304 - 5306
(2011/06/21)
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- SELECTIVE ESTROGEN RECEPTOR MODULATORS CONTAINING A PHENYLSULFONYL GROUP
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The present invention relates to a selective estrogen receptor modulator of formula I or a pharmaceutical acid addition salt thereof; useful, e.g., for treating endometriosis and/or uterine leiomyoma/leiomyomata.
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Page/Page column 45
(2008/06/13)
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- Metallation reactions. Part 35: A change of the regiochemistry in the metallation of (alkylthio)arenes
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The metallation reaction of bromo(alkylthio)benzenes is described. The results show the complementarity of these reactions with the metal-hydrogen exchange reaction. In fact, monometallation of bromo(methylthio)benzenes afforded products substituted in para or meta or ortho to the thioethereal function while bimetallation led to αS,para, αS,meta and αS,ortho disubstituted products. Analogously, the monometallation of 4-bromo-(isopropylthio)benzene afforded para-monosubstituted and ortho,para-disubstituted products.
- Cabiddu, Maria G.,Cabiddu, Salvatore,Cadoni, Enzo,De Montis, Stefania,Fattuoni, Claudia,Melis, Stefana
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p. 3915 - 3920
(2007/10/03)
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- 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
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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.
- Barbero, Margherita,Degani, Iacopo,Diulgheroff, Nicola,Dughera, Stefano,Fochi, Rita,Migliaccio, Mara
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p. 5600 - 5608
(2007/10/03)
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- The Reaction of Alkyl-substituted Thioanisoles with PCl3 and AlCl3: a Route to Benzothiadiphospholobenzothiadiphosphole Derivatives
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The synthesis of benzothiadiphospholobenzothiadiphosphole derivatives starting from alkyl-substituted thioanisoles and PCl3-AlCl3 is reported.The reaction is carried out at reflux in the absence of solvent and the yields are dependent on the starting sulphide.These new heterocycles can be purified by simple filtration on a Florisil column and have been characterized by 1H-, 13C-, (1H)31P-n.m.r. and mass spectroscopy analyses.New unexpected findings are also described.
- Baccolini, Graziano,Mezzina, Elisabetta,Todesko, Paolo Edgardo
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p. 3281 - 3284
(2007/10/02)
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- KINETICS AND MECHANISM OF OXIDATION OF SUBSTITUTED PHENYL METHYL SULPHIDES BY N-BROMOACETAMIDE
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The kinetics of oxidation of several substituted phenyl methyl sulphides by N-bromoacetamide (NBA) in 80percentacetonitrile-20percentwater (v/v) mixture are presented.The reaction is first order with respect to both sulphide and NBA and second order in Hg(II).The rate of the reaction exhibits inverse dependence on both and .Electron-releasing substituents present in the phenyl ring of the sulphides accelerate the rate while electron-withdrawing ones retard it.The results are in accord with a mechanism involving the reaction between NBA-Hg(II) and sulphide-Hg(II) complexes in the slow rate-limiting step affording a sulphonium ion which hydrolyses in a subsequent fast step to the sulphoxide.
- Perumal, Subbu,Alagumalai, Sakkiah,Selvaraj, Sangavanaicker,Arumugam, Natesan
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p. 4867 - 4872
(2007/10/02)
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- Steric Influences on Spin-Lattice Relaxation Rates of Methyl Protons in Substituted Aromatic Molecules
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Proton spin-lattice relaxation rates (R1 values) have been measured at 400 MHz for a series of substituted aromatic compounds to determine the steric effects of ortho substituents on the R1 values of the methyl groups.These values have been interpreted on the basis of differences in the barriers to methyl group rotation caused by the substituent, resulting in changes in the contributions from the dipolar and the spin-rotation relaxation mechanisms.A significant dynamic range of methyl R1 values has been observed, showing that these measurements are sensitive to the steric environment.
- Chazin, Walter J.,Colebrook, Lawrence D.
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p. 597 - 604
(2007/10/02)
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- ONE-POT SYNTHESIS OF ALKYL ARYL TRITHIOCARBONATES FROM BENZENETHIOLS, ALKYL HALIDES, AND CARBON DISULFIDE WITH A PHASE-TRANSFER CATALYST.
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Various alkyl aryl trithiocarbonates may readily be synthesized in good yield at low temperatures such as 20 degree C by allowing trioctylmethylammonium chloride (phase-transfer catalyst) to catalyze reaction of benzenethiols and alkyl halides with carbon disulfide.
- Sugawara,Shirahata,Sato,Sato
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p. 3353 - 3354
(2007/10/02)
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- Synthesis and Lithiation of 2-Alkylthio- and 2-Arylthio-1,3-dithiolanes
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Several 2-alkylthio- and 2-arylthio-1,3-dithiolanes were synthesized by the reaction of 2-ethoxy-1,3-dithiolane with aliphatic and aromatic thiols in the presence of ZnCl2.The lithiation of 2-alkylthio-1,3-dithiolanes with butyllithium in tetrahydrofuran followed by the addition of alkyl halides gave unsymmetrical dialkyl trithiocarbonates in moderately good yields.
- Tanimoto, Shigeo,Oida, Tatsuo,Ikehira, Hideyuki,Okano, Masaya
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p. 1977 - 1978
(2007/10/02)
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- Indenylacetic acid compounds
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4, 5, 6 or 7 Aryl substituted indenyl acetic acids and pharmaceutically acceptable salts, amides and esters thereof. The 4, 5, 6 or 7 aryl substituted indenyl acetic acids have anti-inflammatory, anti-pyretic and analgesic activity. The invention also includes methods for the preparation of these compounds, pharmaceutical compositions and methods of treating inflammation by administering these particular compounds to patients.
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