628-83-1Relevant articles and documents
Thiocyanation and 2-Amino-1,3-thiazole Formation in Water Using Recoverable and Reusable Glycosylated Resorcin[4]arene Cavitands
Husain, Ali A.,Bisht, Kirpal S.
, p. 9928 - 9935 (2020/09/03)
A family of three spatially directional resorcin[4]arene cavitand glycoconjugates (RCGs) have been applied as efficient recoverable and reusable inverse phase transfer catalysts for eco- A nd environmentally friendly thiocyanation and 2-amino-1,3-thiazole formation reactions in water. The results show that RCGs (1 mol %) were capable of hosting and catalyzing various water-insoluble bromo/thiocyanato substrates in water without the use of any co-organic solvents. The recoverability and reusability of RCG catalytic systems, that is, RCG1 and RCG3, were also examined upon a simple extraction of the desired products using DCM or ethyl acetate, followed by subjecting the recovered aqueous solution containing the RCG catalysts to the next reaction cycles.
PEG-DIL-based MnCl42?: A novel phase transfer catalyst for nucleophilic substitution reactions of benzyl halides
Goodajdar, Bijan Mombeni,Akbari, Farideh,Davarpanah, Jamal
, (2019/01/04)
Poly(ethylene glycol) dicationic ionic liquid-based MnCl42? was prepared by nucleophilic substitution of poly(ethylene glycol) dichloride with methylimidazole followed by reaction with MnCl2. The structural properties of the catalyst were systematically investigated using Fourier transform infrared, UV–visible and Raman spectra and thermogravimetric analysis. The application of this catalyst allows the synthesis of a variety of benzyl thiocyanates and azides in high yield under reflux conditions in water. The main advantages of this method are its easy nature, rapidity, environmental benignity and high yields.
Iron-Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers
Exner, Benjamin,Bayarmagnai, Bilguun,Jia, Fan,Goossen, Lukas J.
supporting information, p. 17220 - 17223 (2016/01/25)
Nucleophilic CF3 has been generated by decarboxylation of potassium trifluoroacetate, arguably the most easy-to-handle, inexpensive, and sustainable source of trifluoromethyl groups. Simple iron(II) chloride catalyzes the decarboxylation as well as a subsequent trifluoromethylation of organothiocyanates, resulting in a straightforward synthesis of trifluoromethyl thioethers. The KCN byproduct is absorbed by iron(II) with formation of nontoxic potassium hexacyanoferrate. An analogous trifluoromethylation of aldehydes with trifluoroacetate underlines the synthetic potential of such iron-catalyzed decarboxylative trifluoromethylations.
β-cyclodextrin immobilized onto dowex resin: A unique microvessel and heterogeneous catalyst in nucleophilic substitution reactions
Kiasat, Ali Reza,Zarinderakht, Nasrollah,Sayyahi, Soheil
experimental part, p. 699 - 702 (2012/05/05)
The catalytic activity of β-cyclodextrin immobilized on Dowex resin as an efficient solid-liquid phase transfer catalyst was developed for the synthesis of alkyl thiocyanates and phenacyl derivatives in water. The nucleophilic substitution reactions were performed under mild reaction condition and gave the products in excellent yields. Furthermore, the catalyst could be recycled by facile separation without any loss of activity.
A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate
Meshram,Thakur, Pramod B.,Madhu Babu,Bangade, Vikas M.
experimental part, p. 1780 - 1785 (2012/05/04)
A very rapid, convenient, and general method for the synthesis of α-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl α-halo carbonyls, β-keto tosylates, α-halo β-dicarbonyl, α-tosyl, β-dicarbonyl, alkyl halide, and alkyl tosylates.
Ionic liquid brush as a highly efficient and reusable catalyst for on-water nucleophilic substitutions
Li, Jing,Cao, Jing-Jing,Wei, Jun-Fa,Shi, Xian-Ying,Zhang, Li-Hui,Feng, Jin-Juan,Chen, Zhan-Guo
supporting information; experimental part, p. 229 - 233 (2011/03/20)
A very efficient and reusable catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields. The reaction proceeds smoothly and cleanly without any organic cosolvent or other adductive, and the brush can be reused at least 10 times without noticeable loss of the catalytic activity. The high efficiency, simplicity of product and catalyst isolation, outstanding recyclability, and organic-solvent-free conditions show promise for the use of this catalyst in the laboratory and in industry. A highly efficient and reusable ionic liquid brush catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields without any organic cosolvent or other adductive. The catalyst can be reused at least 10 times without noticeable loss of the catalytic activity. Copyright
A new synthesis of alkane and polyfluoroalkanesulfonyl chlorides
Benfodda, Zohra,Guillen, Franck,Arnion, Helene,Dahmani, Abdelkader,Blancou, Hubert
experimental part, p. 355 - 361 (2010/07/16)
This study describes a new and advantageous procedure for the synthesis of alkanesulfonyl chlorides (2) by the reaction of alkyl thiocyanates (1) with sulfuryl chloride in a mixture of acetic acid and water. The alkanesulfonyl chlorides were obtained in good yields.
Polymer-supported thiocyanate as new, versatile and efficient polymeric reagent for conversion of alkyl halides to corresponding alkyl thiocyanates under mild conditions
Zarchi, Mohammad Ali Karimi
, p. 1299 - 1302 (2008/02/13)
Crosslinked poly(N-methyl-4-vinylpyridinium)thiocyanate [P 4-Me]SCN (II) is prepared easily and is used as a new polymeric reagent for synthesis of alkyl thiocyanates from alkyl halides under mild and nonaqueous conditions. The used polymeric reagent usually can be removing quantitatively and be regenerated.
Efficient conversion of thiols to thiocyanates by in situ generated Ph3P(SCN)2
Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza
, p. 3439 - 3441 (2007/10/03)
A new, novel, rapid and simple method is described for the one-pot conversion of thiols to thiocyanates by use of in situ generated PPh3(SCN)2 at room temperature.
Thiocyanation of alkyl halides with alkyl thiocyanates in the presence of quaternary phosphonium halides
Ohtani, Noritaka,Murakawa, Shigeki,Watanabe, Kohji,Tsuchimoto, Daisuke,Sato, Daiki
, p. 1851 - 1856 (2007/10/03)
Alkyl thiocyanates undergo simple SN2 reactions with the counter ions of quaternary phosphonium salts in nonpolar solvents and thiocyanate ions are liberated as the leaving ion. Depending on the nucleophile, the reaction proceeded irreversibly or reversibly. The reaction of benzyl thiocyanate with azide ions afforded a quantitative yield of benzyl azide. The reactions of alkyl thiocyanates with halide ions gave an equilibrium mixture where the reverse reaction of the alkyl halides produced with the liberated thiocyanate ions took place simultaneously. Thus, thiocyanate-halide exchange reactions between an alkyl thiocyanate and an alkyl halide were possible in the presence of a catalytic amount of a quaternary salt.
