5285-90-5Relevant academic research and scientific papers
N-Thiocyanato-2,10-camphorsultam Derivatives: Design and Applications of Original Electrophilic Thiocyanating Reagents
Gao, Mélissa,Vuagnat, Martin,Jubault, Philippe,Besset, Tatiana
supporting information, (2021/11/30)
The synthesis of bench-stable electrophilic thiocyanating reagents was depicted in two steps from readily available starting materials in good yields. These newly designed electrophilic reagents were successfully applied for the thiocyanation of different
Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thio-/Selenocyanates
Ali, Shamsad,Goswami, Avijit,Kalaramna, Pratibha,Singh, Prasoon Raj
supporting information, p. 4683 - 4689 (2021/09/10)
A straightforward protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition of aryl thio-/selenocyanates with donor-acceptor cyclopropanes (DACs) in the presence of SnCl4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3-cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)-cycloaddition reactions.
Synthesis of (benzenesulfonyl)difluoromethyl thioethers from ((difluoromethyl)sulfonyl)benzene and organothiocyanates generatedin situ
Dai, Jianjun,Shen, Xiao,Wu, Cheng,Xu, Huajian,Xu, Jun
supporting information, p. 7607 - 7610 (2021/09/22)
Easily available aryl and alkyl thiocyanates were converted into the corresponding (benzenesulfonyl)difluoromethyl thioethersviathe direct nucleophilic substitution of ((difluoromethyl)-sulfonyl)benzene under transition metal free conditions. Combined wit
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.
Thiocyanation of aromatic and heteroaromatic compounds with 1-Chloro-1,2-benziodoxol-3-(1H)-one and (Trimethylsilyl)isothiocyanate
Ito, Yuta,Touyama, Akihiro,Uku, Minako,Egami, Hiromichi,Hamashima, Yoshitaka
, p. 1015 - 1018 (2019/09/12)
Thiocyanation of aromatic compounds has been investigated using the combination of 1-chloro-1,2-benziodoxol-3-(1H)-one (1) and (trimethylsilyl)isothiocyanate (TMSNCS). The reaction with electron rich aromatic compounds proceeded smoothly to provide the th
Electrochemical ipso-Thiocyanation of Arylboron Compounds
Dyga, Marco,Hayrapetyan, Davit,Rit, Raja K.,Goo?en, Lukas J.
supporting information, p. 3548 - 3553 (2019/04/26)
An operationally simple electrochemical method for the transition-metal-free ipso-thiocyanation of arylboronic acids and aryl trifluoroborates has been developed. The SCN electrophile is generated in situ by anodic oxidation of thiocyanate anions, which avoids formation of salt waste and prevents unwanted side reactions arising from chemical oxidants. The reaction proceeds regiospecifically, and the scope extends to non-activated aromatic systems. (Figure presented.).
Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers
Gra?l, Simon,Hamze, Clémence,Koller, Thadd?us J.,Knochel, Paul
, p. 3752 - 3755 (2019/02/13)
(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 °C within 1 h in the presence of 5–10 % Cu(OAc)2?H2O to furnish the corresponding polyfunctionalized thioethers in good yields. This electrop
Preparation method for thiocyanide compound
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Paragraph 0082; 0083; 0088; 0089, (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.
