7703-38-0Relevant academic research and scientific papers
Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates
Xing, Wei-Long,Liu, De-Guang,Fu, Ming-Chen
, p. 4593 - 4597 (2021/02/03)
A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility. This journal is
Fe3O4@SiO2-copper sucrose xanthate as a green nanocatalyst for N-, O- and S-arylation
Radfar, Iman,Kazemi Miraki, Maryam,Esfandiary, Naghmeh,Ghandi, Leila,Heydari, Akbar
, (2019/01/04)
Formation of C(sp2)–X bonds was carried out using a Fe3O4@SiO2-copper(I) sucrose xanthate nanoparticle catalyst with the aid of the copper(I) xanthate moiety in the catalyst which was prepared from the reaction between sucrose and carbon disulfide through an alkaline medium via the traditional Zeise approach. Various techniques were employed for the characterization of these novel nanoparticles. Three sorts of heteroatoms, N, O and S, successfully underwent heteroatom arylation to produce secondary or tertiary amines, ethers and thioethers, respectively.
Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides
Liu, Ting,Qiu, Renhua,Zhu, Longzhi,Yin, Shuang-Feng,Au, Chak-Tong,Kambe, Nobuaki
supporting information, p. 3833 - 3837 (2018/12/05)
A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.
One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme
Gholinejad, Mohammad
, p. 4162 - 4167 (2015/06/30)
A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols as starting materials, which is a significant advantage over methods that start from thiols. Alcohols are widely commercially available in a much greater structural diversity than thiols, and they are also nontoxic and not foul-smelling. A reaction mechanism was proposed. A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.
One-pot palladium-catalyzed borrowing hydrogen synthesis of thioethers
Corma, Avelino,Navas, Javier,Rodenas, Tania,Sabater, Maria J.
, p. 17464 - 17471 (2014/01/06)
Palladium on magnesium oxide is able to allow a one-pot reaction to synthesize thioethers from thiols and aldehydes formed in situ from the respective alcohol by means of a borrowing hydrogen method. The reaction is initiated by dehydrogenation of the alcohol to give a palladium hydride intermediate and an aldehyde. The latter reacts with a thiol involving most probably the intermediacy of a thionium ion RCHi£S+R, which can be reduced in situ by the metal hydride to afford thioethers. Lending support: Palladium nanoparticles on MgO catalyze the synthesis of thioethers from thiols and aldehydes formed in situ from alcohols by means of the borrowing hydrogen method (see scheme). Dehydrogenation of the alcohol gives a palladium hydride intermediate and an aldehyde. The latter reacts with a thiol through a thionium ion, which is reduced by the metal hydride to afford thioethers.
TAPC-catalyzed synthesis of thioethers from thiols and alcohols
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Khodadoustan, Nayere
experimental part, p. 2206 - 2210 (2011/10/09)
A new synthesis of thioethers is described. The reaction of aryl alcohols with aryl, heteroaryl, and alkyl thiols in the presence of TAPC as an efficient catalyst affords good to excellent yields of thioethers. Furthermore, the reaction proceeds under metal-free and solvent-free conditions thus represents an interesting complement to known methods for thioether synthesis. A plausible mechanism for this reaction is delineated. Georg Thieme Verlag Stuttgart · New York.
Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor
Prasad,Sekar, Govindasamy
supporting information; experimental part, p. 1008 - 1011 (2011/05/08)
An efficient Cu-catalyzed one-pot approach for the synthesis of unsymmetrical diaryl thioethers using potassium ethyl xanthogenate as a thiol surrogate is developed. This new protocol avoids usage of intricate thiols and makes use of its easily available xanthate as a precursor, and thiol will be generated in situ to prepare the diaryl thioethers through a Cu-catalyzed double arylation. This strategy was further successfully utilized for the synthesis of symmetrical diaryl thioethers, aryl alkyl thioethers, and benzothiazoles. (Figure Presented)
TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides
Bahrami, Kiumars,Khodaei, Mohammad M.,Sheikh Arabi, Mehdi
supporting information; experimental part, p. 6208 - 6213 (2010/11/04)
Figure presented. 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6- tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.
Mild and efficient deoxygenation of sulfoxides to sulfides with triflic anhydride/potassium iodide reagent system
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Karimi, Ahmad
experimental part, p. 2543 - 2546 (2009/04/04)
It was found that the combination of triflic anhydride/potassium iodide was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile at room temperature. It is worth mentioning that this reagent system is chemoselective and tolerates various functional groups, such as alkene, ketone, ester, aldehyde, acid, and oxime. Georg Thieme Verlag Stuttgart.
A novel method for the deoxygenation of sulfoxides with the PPh 3/Br2/CuBr system
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Khedri, Mohammad
, p. 1324 - 1325 (2008/03/18)
It was found that the combination of PPh3/Br2/CuBr was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile under refluxing conditions. It is worth mentioning that this reagent system is chemoselective, tolerating various functional groups such as carbon-carbon double bond and ketone. Copyright
