- Efficient and mild oxidative nuclear thiocyanation of activated aromatic compounds using ammonium thiocyanate and diacetoxyiodobenzene
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A mild and general method for the nuclear thiocyanation of electron rich arenes has been developed by the reaction of NH4SCN with diacetoxyiodobenzene as the oxidant. Copyright Taylor & Francis, Inc.
- Karade,Tiwari,Shirodkar,Dhoot
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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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- 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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- Potassium Persulfate-Mediated Thiocyanation of 2H-Indazole under Iron-Catalysis
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Potassium persulfate-mediated thiocyanation of 2H-indazoles has been developed using ammonium thiocyanate as thiocyanating agent under iron-catalysis at room temperature. 2-Aryl-3-thiocyanato-2H-indazoles are synthesized in good yields with a broad substrates scope. This methodology is also applicable for the selenocyanation of 2H-indazoles. The mechanistic study suggests the reaction probably proceeds through a radical pathway. (Figure presented.).
- Dey, Amrita,Hajra, Alakananda
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- A clay-mediated eco-friendly thiocyanation of indoles and carbazoles
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Indoles 1a-f and carbazoles 3a-c on treatment with ammonium thiocyanate on montmorillonite K10 clay at 80°C furnished the corresponding 3-thiocyanato derivatives 2a-f and 4a-c in good to high yields. Skatole 5 furnished the dimeric oxindole 6, which resulted from autoxidation.
- Chakrabarty, Manas,Sarkar, Sandipan
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- 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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- Temperature-Controlled Chemoselective Synthesis of Thiosulfonates and Thiocyanates: Novel Reactivity of KXCN (X=S, Se) towards Organosulfonyl Chlorides
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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.
- Kalaramna, Pratibha,Goswami, Avijit
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supporting information
p. 5359 - 5366
(2021/10/25)
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- N-doped ZnO as an efficient photocatalyst for thiocyanation of indoles and phenols under visible-light
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In this study, nitrogen-doped ZnO nanorods (N–ZnO NRs) were synthesized via a very simple hydrothermal process, fully characterized, and this photocatalyst was successfully exploited in thiocyanation reactions of indoles and phenols at room temperature under visible light irradiation. Two important classes of aromatic compounds indoles, and phenols using N–ZnO NRs as photocatalyst treated with ammonium thiocyanate as thiocyanation agent formed the corresponding thiocyano compounds in good yields. Nitrogen is one of the most appropriate p-type dopants that is nontoxic, similar to the atomic radius to oxygen, and lower electronegativity and ionization energy than the O atom. Therefore, the N doping converts ZnO into the p-type ZnO semiconductor structure. This potent, simple, and versatile protocol afforded thiocyanation reactions of indole and phenols under visible light. The reactions proceeded through a radical pathway by applying air molecular oxygen as a low cost and environmentally friendly terminal oxidant. The proposed mechanism based on control experiments was thoroughly described. Graphic abstract: [Figure not available: see fulltext.]
- Hosseini-Sarvari, Mona,Sarvestani, Abdollah Masoudi
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p. 903 - 911
(2021/07/17)
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- Visible-light-promoted thiocyanation of sp2C-H bonds over heterogeneous graphitic carbon nitrides
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Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a metal-free heterogeneous photocatalyst for thiocyanation transformations. The reaction proceeds efficiently by utilizing air as a green oxidant under mild reaction conditions, which affords SCN-containing compounds in moderate to excellent yields. Meanwhile, the practicality of this protocol is further demonstrated by the reusability of the mpg-C3N4photocatalyst and the scaled-up reaction. Furthermore, detailed mechanistic studies clearly demonstrate the role of oxygen.
- Chen, Wei,Li, Tingzhen,Peng, Xinwen
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supporting information
p. 14058 - 14062
(2021/08/16)
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- Screening metal-free photocatalysts from isomorphic covalent organic frameworks for the C-3 functionalization of indoles
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The visible-light-driven organic transformation using two-dimensional covalent organic frameworks (2D-COFs) as metal-free heterogeneous photocatalysts is a green and sustainable approach, and it has gained a surge of interest by virtue of the photosensitizer's high crystallinity, abundant porosity, outstanding stability, excellent light-harvesting ability and tunable structure. However, the guiding principle for designing, constructing and selecting COF-based photocatalysts has not been put forward so far. Herein, we contribute a fascinating strategy to guide the acquisition of excellent framework photocatalysts, which is to screen them from a series of isomorphic COFs. As a proof of concept, three new isomorphic pyrene-based 2D-COFs (COF-JLU23, COF-JLU24 and COF-JLU25) with variable linkers were successfully synthesized. In addition to having similar crystallinity and porosity with the same pore size and shape, their absorption, emission, bandgap, energy level, transient photocurrent response and photocatalytic activity could be easily adjustedviaconfiguring different linkers in frameworks. Indeed, COF-JLU24 with electron donor-acceptor characteristics exhibited the best photocatalytic activity among the three isomorphic COFs for C-3 functionalization reactions of indoles, even better than that of the metal-free photocatalyst g-C3N4. More importantly, the screened COF-JLU24 as a metal-free photocatalyst still displayed extensive substrate adaptability and excellent recyclability. We anticipate that this strategy will become a robust rule of thumb for fast access to COF-based photocatalysts. In addition, we still highlight that the present study broadens the applied frontier of COF-based photocatalysts.
- Chen, Xiong,Feng, Xiao,Han, Songjie,Li, Chunzhi,Li, He,Li, Ziping,Liu, Xiaoming,Shao, Pengpeng,Xia, Hong
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supporting information
p. 8706 - 8715
(2020/05/16)
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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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- 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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- Visible-light-induced metal and reagent-free oxidative coupling of: Sp 2 C-H bonds with organo-dichalcogenides: Synthesis of 3-organochalcogenyl indoles
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Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C-H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone at room temperature. This benign protocol allows one to access a wide range of 3-arylselenylindoles, 3-arylthioindoles and even 3-aryltelluroindoles with good to excellent yields. Various functionalities namely, methoxy, and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C-H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene radical cation and a superoxide radical anion. Subsequently, reaction of the radical cation with aryl dichalcogenides provides a diaryl chalcogenyl cation which upon removal of protons gave unsymmetrical 3-indolyl aryl chalcogenides.
- Rathore, Vandana,Kumar, Sangit
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supporting information
p. 2670 - 2676
(2019/06/03)
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- Hypervalent Iodine Mediated Efficient Solvent-Free Regioselective Halogenation and Thiocyanation of Fused N -Heterocycles
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A facile, rapid, metal-free regioselective halogenation and thiocyanation of imidazo[1,2- a ]pyridine/pyrimidine heterocycles has been achieved under solvent-free reaction conditions. Halogenations and thiocyanation of the heterocycles could be accomplish
- Alla, Manjula,Indukuri, Divakar Reddy,Potuganti, Gal Reddy
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supporting information
p. 1573 - 1579
(2019/08/07)
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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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- 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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- 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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- 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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- 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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- 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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- 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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- Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers
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Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions, and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature. Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.
- Zhang, Weijie,Tang, Juntao,Yu, Wenguang,Huang, Qiao,Fu, Yu,Kuang, Guichao,Pan, Chunyue,Yu, Guipeng
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p. 8084 - 8091
(2018/07/30)
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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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- 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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- 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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- 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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- Visible-light-induced aerobic thiocyanation of indoles using reusable TiO2/MoS2 nanocomposite photocatalyst
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TiO2/MoS2 nanocomposite photocatalyst was prepared via simple one-step hydrothermal process. This nontoxic and inexpensive photocatalyst exhibited high activity toward the thiocyanation of indoles under visible light irradiation at room temperature. Simple work-up, good yields, as well as reusability of the catalyst are the major advantages of the present method.
- Wang, Liang,Wang, Cancan,Liu, Wenjie,Chen, Qun,He, Mingyang
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supporting information
p. 1771 - 1774
(2016/04/05)
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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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- 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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- 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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- 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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- 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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- Facile, efficient and eco-friendly synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles
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A concise, two-step eco-friendly approach towards the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles, is reported. The synthesis comprises the oxone-mediated thiocyanation of the starting heterocycles towards intermediate 3-thiocyanato indoles and 2-thiocyanato pyrroles, and their subsequent treatment with sodium azide in 2-propanol/water under zinc bromide promotion.
- Kuhn, Bruna L.,Fortes, Margiani P.,Kaufman, Teodoro S.,Silveira, Claudio C.
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p. 1648 - 1652
(2014/03/21)
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- A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles employing CeCl3·7H 2O in PEG-400
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The use of CeCl3·7H2O in polyethyleneglycol 400 (PEG-400), as an efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato- 1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently substituted starting indoles, 1H,1H′,2,2′-biindoles and N-aryl pyrroles with NH4SCN. The scope and limitations of the transformation were also studied. This journal is the Partner Organisations 2014.
- Fortes, Margiani P.,Bassaco, Mariana M.,Kaufman, Teodoro S.,Silveira, Claudio C.
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p. 34519 - 34530
(2014/11/08)
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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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- 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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- Electrochemical thiocyanation of nitrogen-containing aromatic and heteroaromatic compounds
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An efficient and convenient anodic thiocyanation of nitrogen-containing (hetero)aromatic compounds is described under constant current conditions in the presence of ammonium thiocyanate in methanol at room temperature. We have examined the in situ thiocya
- Fotouhi, Lida,Nikoofar, Kobra
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p. 2903 - 2905
(2013/06/27)
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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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- 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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- 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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- Heterogeneous and catalytic thiocyanation of aromatic compounds in aqueous media
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This article describes a highly efficient heterogeneous catalytic thiocyanation of indoles, substituted anilines (electron rich and electron deficient) and N-substituted aromatic amines in water under mild and green conditions. The reaction of substrates
- Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Mokhlesi, Mohammad,Vahedi, Hoshang,Sajadifar, Sami,Pirveysian, Mahtab
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experimental part
p. 295 - 304
(2012/04/04)
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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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- 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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- 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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- Efficient thiocyanation of indoles using para-toluene sulfonic acid
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Treatment of indoles with ammonium thiocyanate in the presence of para-toluene sulfonic acid afforded the corresponding 3-thiocyano indoles at room temperature in excellent yields.
- Das, Biswanath,Kumar, Avula Satya
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experimental part
p. 337 - 341
(2010/03/30)
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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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- 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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- 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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- 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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