- Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol
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A copper-catalyzed direct and effective synthesis of aryl thiols from aryl iodides using readily available Na 2 S·9H 2 O and 1,2-ethanedithiol was described. A variety of aryl thiols were readily obtained in yields of 76-99%. In this protocol, Na 2 S·9H 2 O was used as ultimate sulfur source, and 1,2-ethanedithiol functioned as an indispensable catalytic reagent.
- Xue, Hongyu,Jing, Bing,Liu, Shasha,Chae, Junghyun,Liu, Yajun
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p. 2272 - 2276
(2017/10/06)
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- SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
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The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017
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Paragraph 0032; 0033; 0063; 0067; 0069; 0070
(2017/09/02)
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- Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
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A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.
- Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun
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supporting information
p. 2205 - 2212
(2015/07/27)
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- Formation, spectroscopic characterization, and solution stability of an [Fe4S4]2+ cluster derived from β-cyclodextrin dithiolate
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The formation and solution properties, including stability in mixed aqueous-Me2SO media, have been investigated for an [Fe 4S4]2+ cluster derived from β-cyclodextrin (CD) dithiolate. Clusters of the type [Fe4S4(SAr) 4]2- (Ar = Ph, C6H4-3-F) are generated in Me2SO by redox reactions of [Fe4S 4(SEt)4]2- with 2 equiv of ArSSAr. An analogous reaction with the intramolecular disulfide of 6A,6 D-(3-NHCOC6H4-1-SH)2-6 A,6D-dideoxy-β-cyclodextrin (14), whose synthesis is described, affords a completely substituted cluster formulated as [Fe 4S4{β-CD-(1,3-NHCOC6H4S) 2}2]2- (15). Ligand binding is indicated by a circular dichroism spectrum and also by UV-visible and isotropically shifted 1H NMR spectra and redox behavior convincingly similar to [Fe 4S4(SPh)4]2-. One formulation of 15 is a single cluster to which two dithiolates are bound, each in bidentate coordination. With there being no proven precedent for this binding mode, we show that the cluster [Fe4S4(S2-m-xyl) 2]2- is a single cubane whose m-xylyldithiolate ligands are bound in a bidentate arrangement. This same structure type was proposed for a cluster formulated as [Fe4S4{β-CD-(1,3-SC 6H4S)2}2]2- (16; Kuroda et al. J. Am. Chem. Soc.1988, 110, 4049-4050) and reported to be water-stable. Clusters 15 and 16 are derived from similar ligands differing only in the spacer group between the thiolate binding site and the CD platform. In our search for clusters stable in aqueous or organic-aqueous mixed solvents that are potential candidates for the reconstitution of scaffold proteins implicated in cluster biogenesis, 15 is the most stable cluster that we have thus far encountered under anaerobic conditions in the absence of added ligand.
- Lo, Wayne,Zhang, Ping,Ling, Chang-Chun,Huang, Shaw,Holm
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p. 9883 - 9892
(2012/11/13)
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- A simple, fast and chemoselective method for the preparation of arylthiols
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An efficient and convenient method for the synthesis of arylthiols by reaction of sulfonyl chlorides with triphenylphosphine in toluene is reported.
- Bellale, Eknath V.,Chaudhari, Mahesh K.,Akamanchi, Krishnacharya G.
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experimental part
p. 3211 - 3213
(2010/03/01)
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- A general and efficient approach to aryl thiols: Cul-catalyzed coupling of aryl iodides with sulfur and subsequent reduction
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A Cul-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K2CO3 at 90 °C. The coupling mixture is directly treated with NaBH4 or triphenylphosphine to afford aryl thiols in good to
- Jiang, Yongwen,Qin, Yuxia,Xie, Siwei,Zhang, Xiaojing,Dong, Jinhua,Ma, Dawei
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supporting information; scheme or table
p. 5250 - 5253
(2009/12/28)
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- Identification of 2-amino-5-(thioaryl)thiazoles as inhibitors of nerve growth factor receptor TrkA
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2-Amino-5-(thioaryl)thiazoles are potent inhibitors of TrkA (e.g., 20h, TrkA IC50 = 0.6 nM) that show anti-proliferative effect in cellular assays. A proposed inhibitor binding mode to TrkA active site is consistent with key SAR observations.
- Kim, Soong-Hoon,Tokarski, John S.,Leavitt, Kenneth J.,Fink, Brian E.,Salvati, Mark E.,Moquin, Robert,Obermeier, Mary T.,Trainor, George L.,Vite, Gregory G.,Stadnick, Linda K.,Lippy, Jonathan S.,You, Dan,Lorenzi, Matthew V.,Chen, Ping
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p. 634 - 639
(2008/09/18)
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- Organic thiol metal-free stabilizers and plasticizers for halogen-containing polymers
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Organic thiol compounds based on pentaerythritol and dipentaerythritol are described herein. More specifically, the compounds of the present invention are mixed esters of pentaerythritol and dipentaerythritol having at least one sulfhydryl group and preferably a plurality of sulfhydryl groups as well as at least one non-thiol-containing group. The organic thiol compounds are utilized to plasticize and/or heat stabilize halogen-containing polymer compositions especially poly(vinyl chloride) compositions. The compositions are substantially free or free of metal-based stabilizers, Lewis acids and terpenes. The compounds of the present invention are ideally utilized in polymers normally susceptible to deterioration and color change which can occur during processing of the polymer or exposure of the polymer to certain environments and surprisingly also serve as excellent plasticizers.
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Page/Page column 5
(2010/02/11)
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- HISTONE DEACETYLASE INHIBITORS
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The present invention provides histone deacetylase inhibitors of general formula (I), process for the preparation of such compounds and uses of the compounds in medicine.
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- THE AQUEOUS PERIODATE OXIDATION OF AROMATIC AND ALIPHATIC CARBOXYLIC ACID DISULFIDES
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The water-soluble carboxylic acid-functionalized aromatic disulfides, 3,3'-dithiodibenzoic acid and 5,5'-dithiodiisophthalic acid (5,5'-dithiodi(1,3-benzenedicarboxylic acid)) were prepared and their rates of periodate oxidation to the sulfonic acids were determined.The reaction is first order in each of the reactants which indicates that the slow step is the initial oxidative cleavage step.These aromatic disulfides are oxidized to the sulfonic acids 4-8 times more slowly than a typical aliphatic disulfide.In all cases, water solubility of the disulfide is of prime importance.The periodate oxidation of two aliphatic carboxylic acid analogs were also examined, however, in these cases, the reactions were multiphasic and intermediate thiosulfinates were observed by 1H NMR along with the sulfonic acids.Key words: Periodate; disulfide; thiosulfonate; sulfonic acid, carboxylic acid, ABTS.
- Evans, Brian J.,Doi, Joyce Takahashi,Musker, W. Kenneth
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- Syntheses of Mercaptobenzoic Acids and Mercaptopyridines Using Elemental Sulfur in the Presence of NaOH-KOH
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Mercaptobenzoic acids and mercaptopyridines were synthesized by using mercaptylation of halogeno compounds with elemental sulfur in the presence of molten salts (NaOH-KOH).This procedure was also applied to the preparation of selenoaryl compounds by using elemental selenium.Based on the behavior of the molten salts and sulfur, Na2S and K2S were considered to be the active species for the mercaptylation.KEYWORDS-mercaptylation; molten salt; o-mercaptobenzoic acid; o-selenobenzoic acid; 2-mercaptopyridine
- Kamiyama, Tsutomu,Enomoto, Saburo,Inoue, Masami
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p. 5184 - 5189
(2007/10/02)
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- An Alternative Synthesis of Tiopinac
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Tiopinac (1) thiepin-3-acetic acid, (1)> has been shown a high degree of antiinflammatory activity and a low incidence of side effects in animals (2).On the basis of results, Tiopinac was chosen for human evaluation in 1978 (2a).
- Thurber, T. Craig,Prince, Anthony,Halpern, Otto
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p. 961 - 965
(2007/10/02)
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