- 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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Read Online
- A two phase electrochemical method for thiocyanation
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A two phase electrochemical method for thiocyanation has been described. Thiocyano derivatives of aromatic amines and phenols and isothiocyano derivatives of substituted amines were obtained in 50-80% yield.
- Krishnan,Gurjar
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Read Online
- A facile synthesis of aryl thiocyanates using sodium perborate
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A simple and convenient synthesis of aryl thiocyanates in high yields using sodium perborate is described.
- Jadhav,Pal,Wadgaonkar,Salunkhe
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Read Online
- N-Thiocyanato-2,10-camphorsultam Derivatives: Design and Applications of Original Electrophilic Thiocyanating Reagents
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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
- Gao, Mélissa,Vuagnat, Martin,Jubault, Philippe,Besset, Tatiana
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supporting information
(2021/11/30)
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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
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supporting information
p. 13166 - 13169
(2021/12/20)
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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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- A highly effective green catalyst Ni/Cu bimetallic nanoparticles supported by dendritic ligand for chemoselective oxidation and reduction reaction
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The highly active Ni/Cu bimetallic nanoparticles (NPs) of the different molar ratios of Ni and Cu (1:1, 1:3, 3:1) assisted by dendritic ligand 2,4,6-Tris (di-4-chlorobenzamido)-1,3-diazine were synthesized successfully confirmed by Scanning Electron Microscopy (SEM), Electron Diffraction X-ray (EDX), X-ray fluorescence spectroscopy (XRF), X-ray diffraction (XRD), and Transmission Electron Microscopy (TEM) analysis. These NPs were studied as a heterogeneous catalyst for the chemoselective oxidation of alcohol to the corresponding aldehyde at 30?min and chemoselective reduction of aromatic nitro substituents to the corresponding amino substituents at 20?min, while the Ni/Cu (3:1) NPs were found to be the most effective among other Ni/Cu?(1:1)?and Ni/Cu?(1:3)?NPs at room temperature under mild conditions. The Ni/Cu (3:1) NPs can be recycled for at least five successive runs with no perceptible decrease in catalytic activity. Graphic abstract: [Figure not available: see fulltext.]
- Islam, Md. Sayedul,Khan, Md. Wahab
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p. 2353 - 2369
(2021/01/07)
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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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- 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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- 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
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Paragraph 0015-0017
(2020/08/06)
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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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- Metal-Free and Visible-Light-Promoted C-3 Thiocyanation of 2-Arylquinolin-4-ones
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A C-3 thiocyanation of 2-aryl-quinolin-4-ones in the presence of eosin-Y and visible light has been developed. The methodology allows easy access to a variety of 2-aryl-3-thiocyano-quinolin-4-ones in moderate to high yields. Regioselective para-thiocyanat
- Chauhan, Parul,Ritu,Preeti,Kumar, Sharvan,Jain, Nidhi
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p. 4334 - 4340
(2019/07/04)
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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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- N -Thiocyanato-dibenzenesulfonimide: A new electrophilic thiocyanating reagent with enhanced reactivity
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A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2 for ketones was used as the catalyst, respectively. It is noteworthy that internal alkenes and styrenes were bifunctionalized giving 1,2-amino thiocyanates in high yields.
- Li, Chengqiu,Long, Pingliang,Wu, Haopeng,Yin, Hongquan,Chen, Fu-Xue
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supporting information
p. 7131 - 7134
(2019/08/07)
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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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- Direct Photocatalytic S-H Bond Cyanation with Green cN Source
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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.
- Guo, Wei,Tan, Wen,Zhao, Mingming,Zheng, Lvyin,Tao, Kailiang,Chen, Deliang,Fan, Xiaolin
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supporting information
p. 6580 - 6588
(2018/05/29)
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- Preparation method for thiocyanide compound
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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.
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Paragraph 0090; 0091; 0096; 0097
(2018/06/16)
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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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supporting information
p. 1576 - 1583
(2018/02/09)
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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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- Rapid and efficient thiocyanation of phenols, indoles, and anilines in 1,1,1,3,3,3-hexafluoro-2-propanol under ultrasound irradiation
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An efficient ultrasound-promoted thiocyanation of phenols, indoles, and anilines in the presence of N-chlorosuccinimide and NH4SCN using 1,1,1,3,3,3-hexafluoro-2-propanol as the solvent has been developed. The major features of the present protocol include the mild reaction conditions, short reaction times, good to excellent yields, and broad substrate scope. Moreover, scale-up synthesis can be achieved and the solvent can be easily recovered and reused.
- Wang, Zhonghao,Wang, Liang,Chen, Qun,He, Ming-yang
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supporting information
p. 76 - 84
(2017/12/28)
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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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- Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles
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An expedient direct and regioselective thiocyanation of phenols, anilines and heterocycles is described. Transformation is realized via the direct C[sbnd]H functionalization under transition metal free conditions at ambient temperature in excellent yields. Method proved to be monoselective and variety of functional groups tolerated the reaction conditions. The practicality of the protocol is demonstrated in gram scale synthesis of a precursor of PPAR δ agonist in excellent yield.
- Mete, Trimbak B.,Khopade, Tushar M.,Bhat, Ramakrishna G.
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supporting information
p. 415 - 418
(2017/01/10)
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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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- Graphene oxide: A promising carbocatalyst for the regioselective thiocyanation of aromatic amines, phenols, anisols and enolizable ketones by hydrogen peroxide/KSCN in water
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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
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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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- Catalytic Thiourea Promoted Electrophilic Thiocyanation of Indoles and Aromatic Amines with NCS/NH4SCN
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A simple and efficient protocol for the electrophilic thiocyanation of indoles and aromatic amines with thiourea/NCS/NH4SCN system has been developed. The major features of the present procedure are the mild conditions, good yields, short reaction times, and the use of inexpensive and readily available organocatalyst. Moreover, N-chlorosuccinimide (NCS) was found to be indispensable, and thiourea could greatly promote the reaction.
- Wang, Cancan,Wang, Zhonghao,Wang, Liang,Chen, Qun,He, Mingyang
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supporting information
p. 1081 - 1085
(2016/11/25)
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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)
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- Determination of the promoting effect of nano SiO2 and H3PO4@nano SiO2 in the thiocyanation of N-containing aromatic compounds under solvent-free conditions
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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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- Zeolite H-Sdusy Powder (Cbv720) as a Recyclable Catalyst for an Efficient Thiocyanation of Aromatic and Heteroaromatic Compounds in Acetonitrile
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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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- Ammonium metavanadate/thiocyanate-triggered electrophilic thiocyanation of aromatic and heteroaromatic compounds in aqueous bisulfate and acetonitrile media
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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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- New data on heteroarene thiocyanation by anodic oxidation of NH 4SCN. the processes of electroinduced nucleophilic aromatic substitution of hydrogen
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Potentiostatic (galvanostatic) electrolysis of NH4SCN in an undivided cell under mild conditions (25 °C, Pt anode, MeCN) was employed to perform the anodic thiocyanation of nitrogen-containing heterocycles with yields up to 95%. The regularitie
- Kokorekin, Vladimir A.,Sigacheva, Vera L.,Petrosyan, Vladimir A.
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supporting information
p. 4306 - 4309
(2014/07/22)
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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
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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
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p. 1378 - 1390
(2015/10/29)
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- 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
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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
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p. 458 - 469
(2014/06/10)
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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
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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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- 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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- Mn(OAc)3-promoted regioselective free radical thiocyanation of indoles and anilines
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Mn(OAc)3-promoted free radical thiocyanations of indoles and arylamines are introduced. Reactions performed under mild conditions give regioselective products in good to excellent yields.
- Pan, Xiang-Qiang,Lei, Mao-Yi,Zou, Jian-Ping,Zhang, Wei
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experimental part
p. 347 - 349
(2009/04/19)
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- Facile method for thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate
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A facile method for direct thiocyanation of activated arenes using iodic acid in combination with ammonium thiocyanate is described.
- Mahajan, Ulhas S.,Akamanchi, Krishnacharya G.
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experimental part
p. 2674 - 2682
(2009/12/04)
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- Synthesis of aryl thiocyanates using Al2O3/MeSO 3H (AMA) as a novel heterogeneous system
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Indoles and various aromatic and heteroaromatic compounds undergo smooth thiocyanation with ammonium thiocyanate in the presence of a mixture of Al 2O3, MeSO3H (AMA) under mild conditions without use of any organic solvent
- Hosseini-Sarvari, Mona,Tavakolian, Mina
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experimental part
p. 318 - 321
(2009/04/16)
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- Thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and I2O5
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Thiocyanation of indoles, pyrrols, and anilines has been efficiently achieved using ammonium thiocyanate as a thiocyanation agent and I2O5 as an oxidant. Copyright Taylor & Francis Group, LLC.
- Wu, Jing,Wu, Guaili,Wu, Longmin
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p. 2367 - 2373
(2008/09/21)
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- DDQ-promoted thiocyanation of aromatic and heteroaromatic compounds
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Thiocyanation of various aromatic and heteroaromatic compounds has been achieved using ammonium thiocyanate in the presence of 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) in methanol solution at room temperature and under reflux condition. The rate of rea
- Memarian, Hamid R.,Mohammadpoor-Baltork, Iraj,Nikoofar, Kobra
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p. 930 - 937
(2008/03/27)
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- Efficient and novel method for thiocyanation of aromatic and heteroaromatic compounds using bromodimethylsulfonium bromide and ammonium thiocyanate
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Various aromatic and heteroaromatic compounds have been efficiently thiocyanated by using a novel combination of bromodimethylsulfonium bromide (BDMS) and ammonium thiocyanate. Georg Thieme Verlag Stuttgart.
- Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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p. 2952 - 2956
(2008/03/12)
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- Ferric(III) chloride-promoted electrophilic thiocyanation of aromatic and heteroaromatic compounds
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Indoles, oxindoles and aromatic amino compounds undergo smooth thiocyanation with ammonium thiocyanate in the presence of anhydrous FeCl 3 in dichloromethane under mild conditions to afford the corresponding 3-indolyl and 4-aryl thiocyanates, respectively, in high yields with excellent selectivity. The use of ferric chloride makes it quite simple, more convenient and practical. This new method offers several advantages such as high conversions, cleaner reaction profiles, short reaction times, and the use of inexpensive and readily available catalyst. Georg Thieme Verlag Stuttgart.
- Yadav,Reddy,Krishna,Suresh Reddy,Narsaiah
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p. 961 - 964
(2007/10/03)
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- Regioselective thiocyanation of aromatic and heteroaromatic compounds using ammonium thiocyanate and oxone
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An efficient and regioselective approach for the thiocyanation of indoles, pyrrole, aromatic amino compounds, and 2-methoxycarbazole has been developed using ammonium thiocyanate as a thiocyanation reagent and oxone as an oxidant.
- Wu, Guaili,Liu, Qiang,Shen, Yinglin,Wu, Wentao,Wu, Longmin
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p. 5831 - 5834
(2007/10/03)
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