- Two-step synthesized sulfonic acid functionalized imidazolium thiocyanate solid acid catalyst for thiocyanation of various electron rich arenes by metal-free method in water
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An eco-friendly, highly efficient, and novel sulfonic acid functionalized imidazolium thiocyanate (Imidazole-SO3H)/SCN and sulfonic acid functionalized imidazolium chloride (Imidazole-SO3H)/Cl solid acid catalyst were successfully synthesized. The structure of catalyst was characterized by various analyses such as FT-IR, 1H NMR and 13C NMR spectroscopy. The thiocyanation reaction of various electron rich arenes such as anilines, indoles, phenols, and other aromatic compounds were selected to show the catalytic performance and efficiency of the as-prepared solid acid catalyst, and excellent yields of the corresponding aryl and heteroaryl thiocyanates derivatives were obtained under metal-free and green conditions in water. In addition, one of the important features of current method is when the thiocyanation reaction is carried out with (Imidazole-SO3H)/SCN, this reagent has a dual role in the reaction, both as thiocyanation agent and as acidic group. On the other hand, (Imidazole-SO3H)/Cl as a catalyst plays just as acidic group in reaction. The current procedure offers advantages such as metal-free and green conditions, simple procedure, the use of a commercially available reagent, simple reaction work-up, ease of separation using simple filtration, and suitable performance in the reusability of the catalyst.
- Naserifar, Zahra,Ramazani, Ali,Rezayati, Sobhan
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- Isoquinolinium-N-sulfonic acid thiocyanate/H2O2 as efficient reagent for thiocyanation of N-bearing (hetero)aromatic compounds
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In the present study, isoquinoline sulfonic acid thiocyanate (isoquinoline-SO3H)SCN and isoquinoline sulfonic acid chloride (isoquinoline-SO3H)Cl as a novel and heterogeneous catalyst were designed and synthesized by a simple and ine
- Rezayati, Sobhan,Kalantari, Fatemeh,Ramazani, Ali,Ezzatzadeh, Elham
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p. 575 - 590
(2021/05/31)
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- Porphyrin-Based Conjugated Microporous Polymer Tubes: Template-Free Synthesis and A Photocatalyst for Visible-Light-Driven Thiocyanation of Anilines
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Conjugated microporous polymers (CMPs) represent an important type of functional materials. In this area, morphological engineering has remained a major challenge. Here, we report the synthesis of porphyrin-based CMP tubes (CMP-1) through a template-free
- Zhang, Pengfei,Yin, Yucheng,Wang, Zhengxin,Yu, Chunyang,Zhu, Yizhou,Yan, Deyue,Liu, Weimin,Mai, Yiyong
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p. 3543 - 3553
(2021/04/12)
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- Selective electrochemical: Para -thiocyanation of aromatic amines under metal-, oxidant- And exogenous-electrolyte-free conditions
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An electrochemical oxidative para-C-H-thiocyanation of aromatic amines has been developed to construct thiocyanato aromatic compounds under metal-, oxidant-, and exogenous-electrolyte-free conditions in an undivided cell. The transformation is compatible
- Zhang, Ying,Gao, Huanjie,Guo, Jiabao,Zhang, Hao,Yao, Xiaoquan
-
supporting information
p. 13166 - 13169
(2021/12/20)
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- Visible light-induced recyclable g-C3N4catalyzed thiocyanation of C(sp2)-H bonds in sustainable solvents
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A metal-free photocatalytic strategy for the preparation of thiocyanated heterocycles from inexpensive NH4SCN has been developed using carbon nitride (g-C3N4) as a general heterogeneous catalyst in a green solvent under an
- Chen, Xiao-Lan,Qu, Ling-Bo,Yu, Bing,Zeng, Fan-Lin,Zhu, Hu-Lin
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supporting information
p. 3677 - 3682
(2021/06/06)
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- Method for inducing thiocyanation of arylamine compound by visible light
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The invention discloses a method for inducing thiocyanation of an arylamine compound by visible light. Specifically, in the atmosphere of oxygen or air, an arylamine compound, an ammonium thiocyanatecompound and copper chloride dihydrate are added into a
- -
-
Paragraph 0083-0086
(2020/08/06)
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- Visible-light-enabled regioselective aerobic oxidative C(sp2)-H thiocyanation of aromatic compounds by Eosin-Y photocatalyst
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Herein, visible-light-enabled regioselective aerobic oxidative C(sp2)-H thiocyanation of aromatic compounds has been developed by employing eosin-Y as effective photocatalyst and oxygen as the green terminal oxidant. This process featured green, efficient and operationally simple. Furthermore, the practicality and utility of this protocol was demonstrated by the gram scale synthesis. Mechanistic studies suggested that this reaction was realized via a photoredox radical pathway.
- Yi, Bing,Wen, Xiaoyong,Yi, Ziqi,Xie, Yanjun,Wang, Qiang,Tan, Jian-Ping
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supporting information
(2020/11/19)
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- Imposing Latency in Ruthenium Sulfoxide-Chelated Benzylidenes: Expanding Opportunities for Thermal and Photoactivation in Olefin Metathesis
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Herein we show the design and synthesis of an electron-rich, sulfoxide-chelated, ruthenium benzylidene. In contrast to previously reported sulfoxide-chelated ruthenium benzylidenes, this complex is more stable in a cis-dichloro conformation and is thus latent in typical olefin metathesis reactions. The complex was characterized by NMR, UV-vis, and X-ray spectroscopy, alongside density functional theory computations. The latent precatalyst could be activated thermally and, depending on the solvent, by UV-C or visible light. In addition, an original "thermo-chromatic" orthogonal sequence was developed, further improved by the use of a thioether chelated complex, where a divergent two-step synthesis can lead to a dihydrofuran or a dihydropyran depending only on the order by which the different stimuli, heat or light, are applied.
- Alassad, Nebal,Goldberg, Israel,Kozuch, Sebastian,Lemcoff, N. Gabriel,Nechmad, Noy B.,Rozenberg, Illya,Segalovich-Gerendash, Gal
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p. 4827 - 4834
(2020/06/01)
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- ARS-TiO2 photocatalyzed direct functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions under visible light
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An ARS-TiO2 photocatalyst has been prepared, by a simple method through stirring a mixture of ARS and TiO2 at room temperature in the dark, to extend the photocatalytic response of titanium dioxide toward the visible light spectrum. The synergic effect of ARS and TiO2 in the photocatalyst system has catalyzed direct C-H functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions. Several aromatic and heteroaromatic scaffolds (2-phenylamino-thiazole, phenol, aniline, indole and pyrrole derivatives) were treated with the thiocyanate anion at room temperature. Herein, the first report on thiocyanation of phenol and synthesis of 2-aminobenzothiazole derivatives under visible light is presented.
- Hosseini-Sarvari, Mona,Hosseinpour, Zeinab,Koohgard, Mehdi,Sarvestani, Abdollah Masoudi
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p. 1401 - 1407
(2020/03/26)
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- Electrochemical and direct C-H methylthiolation of electron-rich aromatics
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The electrochemical-induced C-H methylthiolation of electron-rich aromatics has been accomplished via a three component cross-coupling strategy. Potassium thiocyanate (KSCN) as both the supporting electrolyte and sulfur source and methanol as the methylation reagent are used. This protocol is versatile for various (hetero)aromatic compounds such as aniline, anisole and indole. The reaction proceeds under mild conditions without any metal catalyst, exogenous oxidant and highly toxic sulfur reagent. Importantly, such an electrochemical-induced methylthiolated reaction could be easily scaled up with good efficiency.
- Wu, Yaxing,Ding, Hongliang,Zhao, Ming,Ni, Zhong-Hai,Cao, Jing-Pei
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supporting information
p. 4906 - 4911
(2020/08/25)
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- An electrochemical method for deborylative seleno/thiocyanation of arylboronic acids under catalyst- And oxidant-free conditions
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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.
- He, Dongdong,Yao, Jiaojiao,Ma, Boling,Wei, Jinghao,Hao, Guangguo,Tuo, Xun,Guo, Shengmei,Fu, Zhengjiang,Cai, Hu
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supporting information
p. 1559 - 1564
(2020/03/26)
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- Thiocyanation of aromatic and heteroaromatic compounds with 1-Chloro-1,2-benziodoxol-3-(1H)-one and (Trimethylsilyl)isothiocyanate
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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
- Ito, Yuta,Touyama, Akihiro,Uku, Minako,Egami, Hiromichi,Hamashima, Yoshitaka
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p. 1015 - 1018
(2019/09/12)
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- Electrochemical ipso-Thiocyanation of Arylboron Compounds
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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.).
- Dyga, Marco,Hayrapetyan, Davit,Rit, Raja K.,Goo?en, Lukas J.
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supporting information
p. 3548 - 3553
(2019/04/26)
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- Visible light thiocyanation of: N -bearing aromatic and heteroaromatic compounds using Ag/TiO2 nanotube photocatalyst
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In this study, Ag/TiO2 nanotubes (Ag/TNT) were synthesized via simple hydrothermal process, and this photocatalyst was successfully exploited in thiocyanation reactions at room temperature under visible light irradiation. Four classes of important heterocyclic compounds including indole, aniline, pyrrole and 2-amino thiazole derivatives via Ag/TNT treated with ammonium thiocyanate formed the corresponding thiocyano compounds in moderate to excellent yields. Plasmonic property and catalytic performance of Ag nanoparticles (which mainly deposited on the surface of TNT) in absorbing species containing sulfur atoms were key components for the reactions to proceed. This potent, simple and versatile protocol reported for the first time afforded thiocyanation reactions of aniline, pyrrole and 2-amino thiazole derivatives under visible light. The reactions proceeded through a radical pathway by applying air molecular oxygen as a low-cost and environmentally friendly terminal oxidant.
- Hosseini-Sarvari, Mona,Hosseinpour, Zeinab,Koohgard, Mehdi
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supporting information
p. 19237 - 19244
(2018/11/27)
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- Novel Br?nsted acidic ionic liquids catalyzed one-pot reaction of highly green regioselective thiocyanation of N-containing aromatic and heteroaromatic compounds at room temperature
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In this method, a novel Br?nsted acidic ionic liquid silica-supported pyridinium sulfonic acid thiocyanate {SiO2@[Pyridine-SO3H]SCN} and sulfonic acid-functionalized pyridinium chloride {[PSA]Cl} were easily synthesized and character
- Sajjadifar, Sami,Mansouri, Ghobad,Nikseresht, Ahmad,Kakaei Azani, Fatemeh
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p. 294 - 307
(2018/02/06)
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- A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions
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A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell. This strategy is versatile for various (hetero)aromatic compounds such as indole, pyrrole, aniline and anisole under mild conditions without any catalyst or oxidant. Readily available salts NH4SCN and KSeCN are employed respectively as the sole reagent.
- Zhang, Xing,Wang, Chenguang,Jiang, Hong,Sun, Linhao
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p. 22042 - 22045
(2018/06/26)
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- 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
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Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.
- Khosravi, Kaveh,Naserifar, Shirin
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supporting information
p. 6584 - 6592
(2018/10/05)
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- Catalyst and additive-free regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with elemental sulfur/selenium and TMSCN
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A regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with TMSCN and elemental sulfur/selenium was demonstrated under catalyst-free and additive-free conditions. Dimethyl sulfoxide (DMSO) was employed as the mild oxidant as well as the solvent. The reaction is operationally simple and scalable with a broad substrate scope.
- Feng, Chengtao,Peng, Ya,Ding, Guangrong,Li, Xiangxiao,Cui, Chang,Yan, Yizhe
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supporting information
p. 13367 - 13370
(2018/12/13)
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- N-Thiocyanatosaccharin: A "sweet" Electrophilic Thiocyanation Reagent and the Synthetic Applications
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N-Thiocyanatosaccharin (R1) was readily prepared from the sweet additive Saccharin in two steps with a 71% overall yield. By applying this new reagent to diverse nucleophiles such as benzothiophenes, indoles, oxindoles, aromatic amines, phenols, β-keto carbonyl compounds, and aromatic ketones, a novel electrophilic thiocyanation reaction was achieved with high yields (up to 99%). The potential recycling of Saccharin, the wide scope of substrates, and the mild reaction conditions made this protocol much more practical.
- Wu, Di,Qiu, Jiashen,Karmaker, Pran Gopal,Yin, Hongquan,Chen, Fu-Xue
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p. 1576 - 1583
(2018/02/09)
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- Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics
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A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O2 as the oxidant. The combination of Cu(OTf)2, N,N,N′,N′-tetramethylethylenediamine (TMEDA) and BF3·Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups.
- Jiang, Huanfeng,Yu, Wentao,Tang, Xiaodong,Li, Jianxiao,Wu, Wanqing
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p. 9312 - 9320
(2017/09/22)
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- Synthesis of perfluoroalkyl thioethers from aromatic thiocyanates by iron-catalysed decarboxylative perfluoroalkylation
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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.
- Exner, Benjamin,Bayarmagnai, Bilguun,Matheis, Christian,Goossen, Lukas J.
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supporting information
p. 89 - 93
(2017/06/23)
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- One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)
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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.
- Xu, Lijun,Wang, Hongyu,Zheng, Changwu,Zhao, Gang
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p. 6057 - 6066
(2017/09/23)
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- An efficient method for thiocyanation of aromatic and heteroaromatic compounds using cyanuric chloride and ammonium thiocyanate under conventional and nonconventional conditions
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Highly efficient thiocyanation of aromatic and heteroaromatic compounds has been accomplished by using cyanuric chloride (NCCl)3/NH4SCN in dichloromethane under conventional and ultrasonic-assisted conditions. Sonicated reactions rea
- Venkanna,Rajanna,Kumar, M. Satish,Venkateswarlu,Ali, M. Moazzam
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p. 237 - 240
(2016/01/20)
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- Nitrogen Dioxide Catalyzed Oxidative Thiocyanation of Arenes with Ambient Air as the Terminal Oxidant
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NO2 is an effective catalyst for the oxidative thiocyanation of arenes. This unique catalyst is inexpensive and separated easily from the final products because of its low boiling point. The mild reaction conditions allow a series of arenes and thiophenes to be thiocyanated smoothly in moderate to high yields. A preliminary mechanistic investigation suggests that the present reaction may proceed through a radical pathway.
- Ren, Yun-Lai,Wang, Wenhui,Zhao, Bo,Tian, Xinzhe,Zhao, Shuang,Wang, Jianji,Li, Fuwei
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p. 3361 - 3366
(2016/11/16)
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- Graphene oxide: A promising carbocatalyst for the regioselective thiocyanation of aromatic amines, phenols, anisols and enolizable ketones by hydrogen peroxide/KSCN in water
-
Graphene oxide (GO), as a heterogeneous carbocatalyst, catalyzes the direct thiocyanation of a variety of arenes including aromatic amines, phenols, anisols and carbonyl compounds that possessing α-hydrogen in the presence of hydrogen peroxide and KSCN in water as a green media. This procedure is chemoselective, avoids the use of precious metals and toxic solvents and has a broad substrate scope. Easy removal from the reaction mixture and recyclability with no loss of activity are the key features of graphene oxide in this catalytic system.
- Khalili, Dariush
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p. 2547 - 2553
(2016/03/19)
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- Regioselctive thiocyanation of aromatic and heteroaromatic compounds using a novel br?nsted acidic ionic liquid
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A convenient procedure for the preparation of 1-(1-Propylsulfonic)-3- methylimidazolium thiocyanate as a novel Bronsted acidic ionic liquid thiocyanation agent and highly efficient heterogeneous catalytic is described. This catalyst is used in regioselective thiocyanation of indoles, anilines, pyrroles and their derivatives (aromatic and heteroaromatic organic compounds) in the presence of H2O2 as a mild and oxidant in EtOH:H2O (1:1 v/v). These reactions are performed under mild and simple conditions and give regioselective products in high yields and short reaction time.
- Rezayati, Sobhan,Sheikholeslami-Farahani, Fatemeh,Hossaini, Zinatossadat,Hajinasiri, Rahimeh,Abad, Saeid Afshari Sharif
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p. 720 - 727
(2016/12/16)
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- Thiocyanation of aromatic and heteroaromatic compounds using polymer-supported thiocyanate ion as the versatile reagent and ceric ammonium nitrate as the versatile single-electron oxidant
-
ABSTRACT: Indoles, pyrrole aniline derivatives and aromatic amino compounds undergo smooth thiocyanation with cross-linked poly (4-vinylpyridine) supported thiocyanate ion, [P4-VP]SCN in the presence of ceric ammonium nitrate (CAN) as a versati
- Karimi Zarchi, Mohammad Ali,Banihashemi, Reza
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p. 282 - 295
(2016/06/01)
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- Iron-Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers
-
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.
- Exner, Benjamin,Bayarmagnai, Bilguun,Jia, Fan,Goossen, Lukas J.
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supporting information
p. 17220 - 17223
(2016/01/25)
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- Zeolite H-Sdusy Powder (Cbv720) as a Recyclable Catalyst for an Efficient Thiocyanation of Aromatic and Heteroaromatic Compounds in Acetonitrile
-
Thiocyanation of various aromatic and heteroaromatic compounds has been studied using Zeolite H-SDUSY Powder (CBV720) as catalyst and ammonium thiocyanate (NH4SCN) as thiocyanation reagent in acetonitrile medium. Reactions afforded good yields of products under stirred conditions at reflux temperature. Reactions underwent enhancements under sonication (using an ultrasonic probe of 24 kHz frequency) and microwave irradiation. The use of ultrasound decreased the reaction times from (7-12 h) to few minutes (70-150 min). The use of microwave irradiation much more effectively enhanced the reaction rates than sonicated and conventional protocols used in this study.
- Chary, V. Sudhakar,Krishnaiah,Kumar, M. Satish,Rajanna
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p. 1146 - 1153
(2015/08/04)
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- AlCl3-Promoted Thiocyanation of N-Containing Aromatic and Heteroaromatic Compounds Under Solvent-Free Conditions
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Aluminum chloride/Ammonium thiocyanate (AlCl3/NH4SCN) was found to be an effective system for the thiocyanation of some arylamines and indoles to afford the corresponding thiocyanated adducts at room temperature under solvent-free conditions. The efficacy of this combined reagent was also examined in the thiocyanation of pyrrole and isatin. A plausible mechanism of thiocyanation has also been suggested.
- Nikoofar, Kobra,Gorji, Samareh
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p. 1138 - 1145
(2015/08/04)
-
- Determination of the promoting effect of nano SiO2 and H3PO4@nano SiO2 in the thiocyanation of N-containing aromatic compounds under solvent-free conditions
-
Silica nanoparticles/ammonium thiocyanate (nano SiO2/NH4SCN) and H3PO4 embedded on nano silica (H3PO4@nano SiO2) in the presence of NH4SCN were found to be effective systems for the thiocyanation of some arylamines and indoles to afford their corresponding thiocyanated adducts at 70C under solventfree conditions. The recovery and reusability of nano SiO2 as a prompting system have been investigated. A simple procedure for the synthesis of H3PO4@nano SiO2 has also been represented. In addition, a plausible mechanism of thiocyanation has also been suggested.
- Nikoofar, Kobra,Gorji, Samareh
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p. 178 - 186
(2015/10/20)
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- Catalyst-Free Regioselective C-3 Thiocyanation of Imidazopyridines
-
A direct and straightforward approach for highly regioselective thiocyanation of imidazoheterocycles through sp2 C-H functionalization has been realized at room temperature. Various C-3 thiocyanated imidazopyridines are formed in moderate to go
- Yang, Daoshan,Yan, Kelu,Wei, Wei,Li, Guoqing,Lu, Shenglei,Zhao, Caixia,Tian, Laijin,Wang, Hua
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p. 11073 - 11079
(2015/11/18)
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- Potassium thiocyanate as source of cyanide for the oxidative α-cyanation of tertiary amines
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Oxidation at the sulfur of the safe-to-handle potassium thiocyanate releases cyanide units that are trapped in the presence of co-oxidized tertiary amines to form α-amino nitriles. These cyanations work in aqueous solutions and do not require a catalyst,
- Wagner, Alexander,Ofial, Armin R.
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p. 2848 - 2854
(2015/03/18)
-
- Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ
-
A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts. This strategy enables the introduction of difluoromethylthio groups - a largely unexplored substituent with highly promising properties - into drug-like molecules. A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts.
- Bayarmagnai, Bilguun,Matheis, Christian,Jouvin, Kvin,Goossen, Lukas J.
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p. 5753 - 5756
(2015/06/10)
-
- Synthesis of Aryl Tri- and Difluoromethyl Thioethers via a C H-Thiocyanation/Fluoroalkylation Cascade
-
An AlCl3-catalyzed C H thiocyanation was discovered and combined with a Langlois-type trifluoromethylation to afford aryl trifluoromethyl thioethers directly from arenes, N-thiocyanatosuccinimide (NTS) and Ruppert-Prakash reagent. An analogous combination with a copper-mediated difluoromethylation gives access to aryl difluoromethyl thioethers. Both processes proceed with exceptional regioselectivity for the most electron-rich, sterically least hindered position of the arene. The sulfur and fluoroalkyl groups originate from different sources, so that the use of expensive, preformed fluoroalkylthiolation reagents is avoided. Perfectly formed: An AlCl3-catalyzed C H thiocyanation was combined with a Langlois-type trifluoromethylation to afford aryl trifluoromethyl thioethers directly from arenes, N-thiocyanatosuccinimide, and TMS-CF3 (see scheme). An analogous combination of the thiocyanation with a copper-mediated difluoromethylation gives access to aryl difluoromethyl thioethers. The sulfur and fluoroalkyl groups originate from different sources, so that preformed fluoroalkylthiolation reagents are avoided.
- Jouvin, Kévin,Matheis, Christian,Goossen, Lukas J.
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supporting information
p. 14324 - 14327
(2015/10/05)
-
- An efficient and regioselective thiocyanation of aromatic and heteroaromatic compounds using cross-linked poly (4-vinylpyridine)-supported thiocyanate as a versatile reagent and potassium peroxydisulfate as a strong oxidizing agent
-
A green and regioselective thiocyanation of aromatic and heteroaromatic compounds has been achieved via a simple protocol using cross-linked poly (4-vinylpyridine)-supported thiocyanate ion, [P4-VP]SCN, as a versatile polymeric reagent and potassium persulfate as a strong oxidizing agent, under heterogeneous conditions.Various indoles, phenol and aniline derivatives, and pyrroles were transformed into their corresponding aryl thiocyanates in high to excellent yields. This procedure offers advantages such as short reaction time, simple reaction work-up, and the polymeric reagents can be regenerated and reused for several times without significant loss of their activity.
- Karimi Zarchi,Banihashemi
-
p. 458 - 469
(2014/06/10)
-
- Ammonium metavanadate/thiocyanate-triggered electrophilic thiocyanation of aromatic and heteroaromatic compounds in aqueous bisulfate and acetonitrile media
-
The ammonium metavanadate/thiocyanate system is used as an efficient reagent for regioselective thiocyanation of aromatic and hetero aromatic compounds under conventional and nonconventional conditions such as ultrasonically assisted and microwave-assisted reactions. The reactions proceeded smoothly and afforded good yields of products with high regioselectivity. Longer reaction times (about 8 h) observed under conventional conditions were reduced to 0.5 h/30 min under sonication and to 90 s in the case of microwave-assisted reactions.
- Venkatesham,Rajendar Reddy,Rajanna,Veerasomaiah
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p. 606 - 612
(2015/10/19)
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- Green and Efficient Method for Thiocyanation of Aromatic and Heteroaromatic Compounds Using Cross-linked Poly (4-Vinylpyridine) Supported Thiocyanate Ion as Versatile Reagent and Oxone as Mild Oxidant
-
A green and efficient regioselective thiocyanation of indoles, anilines and pyrrole has been achieved via a simple protocol using cross-linked poly (4-vinylpyridine) supported thiocyanate ion, [P4-VP]SCN, as a versatile polymeric reagent and ox
- Ali, Mohammad,Zarchi, Karimi,Banihashemi
-
p. 1378 - 1390
(2015/10/29)
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- 1-methyl-3-(2-(Sulfooxy)Ethyl)-1H-imidazol-3-ium thiocyanate as a novel, green, and efficient bronsted acidic ionic liquid-promoted regioselective thiocyanation of aromatic and heteroaromatic compounds at room temperature
-
An efficient and simple method for the preparation of 1-methyl-3-(2- (sulfooxy)ethyl)-1H-imidazol-3-ium thiocyanate ([Msei]SCN) as a Bronsted acidic ionic liquid (BAIL) is described, and it is used in the highly efficient regioselective thiocyanation of aromatic and heteroaromatic compounds via a green and simple protocol. [Msei]SCN as a novel IL and thiocyanation agent, H2O2 as a mild and environmentally friendly oxidant, and H2O:ethanol(1:4) as a solvent were used. This procedure provided the target thiocyanates in high yield and very short reaction time. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional figures.]
- Sajjadifar, Sami,Hosseinzadeh, Hossein,Ahmadaghaee, Saied,Rezaee Nezhad, Eshagh,Karimian, Saaid
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p. 333 - 342
(2014/03/21)
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- 2,2-Azobenzothiazole as a new recyclable oxidant for heterogeneous thiocyanation of aromatic compounds with ammonium thiocyanate
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A simple synthesis of thiocyanated aromatics has been developed by using heteroaromatic azo compounds such as 2,2′-azobenzothiazole as a mild and heterogeneous oxidant. The reactions proceed at room temperature with good regioselectivity. The hydrazine by
- Iranpoor, Nasser,Firouzabadi, Habib,Shahin, Rezvan,Khalili, Dariush
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experimental part
p. 2040 - 2047
(2012/06/16)
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- Simple and highly efficient catalytic thiocyanation of aromatic compounds in aqueous media
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Two simple, mild, and efficient procedures for the thiocyanation of N-heterocycles, substituted anilines (electron-rich and electron-deficient), and N-substituted aromatic amines at room temperature are reported (Table3). The first uses H2Osub
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Mokhlesi, Mohmmad,Panah, Fateme Derakhshan,Sajjadifar, Sami
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experimental part
p. 106 - 114
(2012/02/14)
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- Silica-bonded vanadic acid [SiO2-VO(OH)2] as a heterogeneous and recyclable catalyst for thiocyanation of organic compounds in aqueous media at room temperature
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Silica vanadic acid (in which vanadium oxytrichloride has been supported on silica) is applied as an efficient, reusable and heterogeneous catalyst for the thiocyanation of heterocycles, substituted anilines (electron-rich and electron-deficient) and N-su
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Safaiee, Maliheh,Mokhlesi, Mohammad,Donyadari, Elmira,Shiri, Morteza,Kruger, Hendrik Gerhardus
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experimental part
p. 34 - 38
(2012/08/28)
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- Citric acid as a trifunctional organocatalyst for thiocyanation of aromatic and heteroaromatic compounds in aqueous media
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A green and simple procedure for the thiocynation of aromatic and heteroaromatic rings in the presence of a catalytic amount of citric acid in water are described. The reactions proceed in high yields, with short reaction times and under mild conditions.
- Khazaei, Ardeshir,Zolfigol, Mohammad Ali,Mokhlesi, Mohmmad,Pirveysian, Mahtab
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experimental part
p. 427 - 432
(2012/06/16)
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- Efficient and novel method for thiocyanation of aromatic compounds using trichloroisocyanuric acid/ammonium thiocyanate/wet SiO2
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An efficient and novel method for thiocyanation of aromatic and heteroaromatic compounds using trichloroisocyanuric acid/ammonium thiocyanate/wet SiO2 is described. Copyright Taylor & Francis Group, LLC.
- Akhlaghinia, Batool,Pourali, Ali-Reza,Rahmani, Marzieh
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experimental part
p. 1184 - 1191
(2012/04/04)
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- Microwave-assisted neat reaction technology for regioselective thiocyanation of substituted anilines and indoles in solid media
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An efficient and solvent -free approach for regioselective thiocyanation of various substituted anilines and indoles is described. The reaction performed both on and off the alumina surface under microwave conditions. Microwave irradiation reactions under
- Murthya,Govindha,Diwakara,Nagalakshmia,Venub
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experimental part
p. 292 - 297
(2012/01/03)
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- Poly[4-diacetoxyiodo] styrene-promoted thiocyanation of aromatic ethers, anilines, and indoles
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Chemical Equation Presented Thiocyanation of aromatic ethers, anilines, and indoles have been achieved using ammonium thiocyanate in the presence of poly[4-diacetoxyiodo] styrene (PDAIS) in CH3CN at room temperature. Copyright Taylor & Francis Group, LLC.
- Wu, Liqiang,Chao, Shujun,Wang, Xiao,Yan, Fulin
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experimental part
p. 304 - 310
(2011/04/22)
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- A simple and efficient thiocyanation of indoles, anilines and keto compounds catalyzed by a polystyrene resin amberlyst-15
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Thiocyanation of various aromatic, heteroaromatic and enolizable ketone compounds has been achieved with ammonium thiocyanate in presence of polystyrene cation exchange resin, Amberlyst-15. All the reactions were carried out in acetonitrile at room temper
- Lenin, Racha,Raju, Rallabandi M.
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experimental part
p. 392 - 395
(2011/04/12)
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- A new application for diethyl azodicarboxylate: Efficient and regioselective thiocyanation of aromatics amines
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Highly regioselective thiocyanations of indoles, anilines and pyrrole are achieved via an efficient and simple protocol using NH4SCN and diethyl azodicarboxylate (DEAD) as a mild oxidant.
- Iranpoor, Nasser,Firouzabadi, Habib,Khalili, Dariush,Shahin, Rezvan
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experimental part
p. 3508 - 3510
(2010/08/20)
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- Anodic thiocyanation of mono-and disubstituted aromatic compounds
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The in situ and environmentally friendly thiocyanation (no use of toxic oxidizing agents) electrochemical thiocyanation of aromatic compounds involving various derivatives of anisole and aniline to afford aromatic thiocyanates have been studied in organic
- Gitkis, Anna,Becker, James Y.
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experimental part
p. 5854 - 5859
(2011/01/07)
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