- 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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- 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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- 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 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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- Method for preparing N,N-diethyl-4-thiocyanatoaniline
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The invention aims at providing a method for preparing N,N-diethyl-4-thiocyanatoaniline. The method for preparing N,N-diethyl-4-thiocyanatoaniline comprises the following steps of: dissolving N,N-diethyl aniline and thiocyanate into an organic solvent to
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Paragraph 0026; 0027; 0028; 0029; 0030; 0031; 0032-0045
(2017/08/27)
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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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- 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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- 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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- 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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- 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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- 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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- IBX: A novel and versatile oxidant for electrophilic thiocyanation of indoles, pyrrole and arylamines
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The direct thiocyanation of indoles and pyrrole with ammonium thiocyanate has been achieved using o-iodoxybenzoic acid (IBX) under mild and neutral conditions to produce indol-3-yl and pyrrol-2-yl thiocyanates, respectively, in excellent yields and with h
- Yadav, Jhillu S.,Subba Reddy, Basi V.,Krishna, B. Bala Murali
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experimental part
p. 3779 - 3782
(2009/06/06)
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- 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane Bis(tetrafluoroborate) as Novel and Versatile Reagent for the Rapid Thiocyanation of Indoles, Azaindole, and Carbazole
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Selectfluor is found to catalyze efficiently the electrophilic thiocyanation of indoles and pyrrole with ammonium thiocyanate under mild and neutral conditions to produce the corre-sponding 3-indolyl and 2-pyrrolyl thiocyanates, respectively, in excellent
- Yadav,Reddy, B. V. Subba,Reddy, Y. Jayasudhan
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p. 652 - 653
(2008/12/21)
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- Understanding reactivity patterns of the dialkylaniline radical cation
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N,N-Dimethylaniline and N,N-diethylaniline react with Cu2+ to form the corresponding amine radical cations. The radical cations were characterized by their absorption spectra. In the absence of any nucleophiles, the radical cations dimerize to give tetraalkylbenzidines, and this reaction can be monitored by absorption spectroscopy, In the presence of nucleophiles such as Cl, Br, or SCN, the radical cations undergo nucleophilic substitution to give para-substituted dialkylanilines in good yields.
- Kirchgessner, Micha,Sreenath, Kesavapillai,Gopidas, Karical R.
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p. 9849 - 9852
(2007/10/03)
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