3226-41-3Relevant academic research and scientific papers
Temperature-Controlled Chemoselective Synthesis of Thiosulfonates and Thiocyanates: Novel Reactivity of KXCN (X=S, Se) towards Organosulfonyl Chlorides
Kalaramna, Pratibha,Goswami, Avijit
supporting information, p. 5359 - 5366 (2021/10/25)
An efficient chemoselective protocol has been developed for the synthesis of thiosulfonates and thiocyanates by employing cost effective and commercially available organosulfonyl chlorides with potassium thio-/selenocyanate. The strategy offered the thiosulfonates and thiocyanates selectively by tuning the equivalents of KSeCN and optimizing the reaction temperature. On the other hand, thiosulfonates were obtained as sole products when organosulfonyl chlorides were treated with KSCN. Furthermore, the syntheses of diarylthioethers and aryl(heteroaryl) thioethers were carried out as a part of synthetic application of newly prepared arylthiocyanates.
Straightforward Access to Thiocyanates via Dealkylative Cyanation of Sulfoxides
Todorovi?, Uro?,Klose, Immo,Maulide, Nuno
supporting information, p. 2510 - 2513 (2021/04/13)
Thiocyanates, versatile building blocks in organic synthesis, are shown to be easily accessible via an interrupted Pummerer reaction of sulfoxides. This facile dealkylative functionalization proceeds under mild conditions through electrophilic activation of the sulfoxide partner. The resulting thiocyanate itself can serve as a handle for diversification in a straightforward one-pot procedure.
Selectfluor-initiated cyanation of disulfides to thiocyanates
Zhou, Pengpeng,Chen, Chuan,Li, Shubai
, p. 376 - 380 (2020/02/13)
A Selectfluor-initiated cyanation of disulfides to thiocyanates has been developed. In this process, Selectfluor was employed as the oxidant and trimethylsilyl cyanide was used as the cyanation reagent. It provides an eco-friendly and simple way to synthesize the thiocyanates.
An electrochemical method for deborylative seleno/thiocyanation of arylboronic acids under catalyst- And oxidant-free conditions
He, Dongdong,Yao, Jiaojiao,Ma, Boling,Wei, Jinghao,Hao, Guangguo,Tuo, Xun,Guo, Shengmei,Fu, Zhengjiang,Cai, Hu
supporting information, p. 1559 - 1564 (2020/03/26)
An electrochemical deborylative seleno/thiocyanation of arylboronic acids has been well established to synthesize the corresponding aryl seleno/thiocyanates with good functional group tolerance under ambient conditions. A gram-scale reaction has been performed to highlight the advantages of the protocol. Preliminary mechanistic studies indicate that the oxidation of the seleno/thiocyanate anion occurs prior to that of the arylboronic acid substrate in galvanostatic mode, and that free radicals are involved in the process.
Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates
Chen, Yang,Qi, Hongyi,Chen, Ning,Ren, Demin,Xu, Jiaxi,Yang, Zhanhui
, p. 9044 - 9050 (2019/08/12)
Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the sulfur radical cation and cyano radical are both involved. They combine to deliver cyanosulfonium, an intermediate toward thiocyanate after dealkylation. Alternatively, a nucleophilic mechanism is also possible. Our dealkyaltive cyanation is also efficient in synthesizing thiocyanates with strongly electrophilic functionalities.
Preparation method for thiocyanide compound
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Paragraph 0130; 0131; 0136; 0137, (2018/06/16)
The invention discloses a preparation method for a thiocyanide compound. The preparation method comprises the following steps: taking a sulfhydryl compound, thiocyanate as raw materials, taking rose-bengal, eosine Y or eosin B as a catalyst, performing illumination, generating a thiocyanide compound after the illumination reaction. According to the preparation method provided by the invention, thiocyanide is decomposed into thiocyanate ions; the sulfhydryl compound generates sulfhydryl radical under the action of light and the catalyst, and the sulfhydryl radical is used for attacking carbon atoms in thiocyanate ions to obtain a intermediate; sulfide is removed from the intermediate to obtain the thiocyanide compound. The rose-bengal, the eosine Y or the eosin B used by the method containno heavy metal ion, and the adverse effect on the performance of the thiocyanide compound by the heavy metal ion residue is avoided; in addition, the catalyst is easily removed, so that a favorable condition is provided for the preparation of the thiocyanide compound with higher purity.
Direct Photocatalytic S-H Bond Cyanation with Green cN Source
Guo, Wei,Tan, Wen,Zhao, Mingming,Zheng, Lvyin,Tao, Kailiang,Chen, Deliang,Fan, Xiaolin
supporting information, p. 6580 - 6588 (2018/05/29)
Herein we report a novel C-S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S-H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C-S bond of SCN- to deliver the green CN sources is demonstrated. This transformation features nontoxic and inexpensive CN sources, available starting materials, metal-/base-/ligand-/peroxide-free, high step economy and mild conditions. It leads to the construction of various thiocyanates and some medicinally and biologically active thiocyanate-containing molecules.
Synthesis of perfluoroalkyl thioethers from aromatic thiocyanates by iron-catalysed decarboxylative perfluoroalkylation
Exner, Benjamin,Bayarmagnai, Bilguun,Matheis, Christian,Goossen, Lukas J.
supporting information, p. 89 - 93 (2017/06/23)
Easily available aryl and heteroaryl thiocyanates were converted into the corresponding perfluoroalkyl thioethers via decarboxylation of potassium perfluoroalkylcarboxylates, catalysed by the inexpensive and environmentally benign iron(III) chloride.
One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)
Xu, Lijun,Wang, Hongyu,Zheng, Changwu,Zhao, Gang
, p. 6057 - 6066 (2017/09/23)
An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.
Transition-metal-free synthesis of thiocyanato- or nitro-arenes through diaryliodonium salts
Li, Xiao-Hua,Li, Liang-Gui,Mo, Xue-Ling,Mo, Dong-Liang
, p. 963 - 970 (2016/07/07)
A transition-metal-free approach to facile synthesis of thiocyanato- and nitro-arenes was developed from KSCN (potassiumthiocyanate) or NaNO2with diaryliodonium salts in good yields under mild conditions. The reaction was compatible with a variety of sensitive functional substituents such as halides and nitro and ester groups. The usefulness of arylation products has been realized. (Formula Present).
