- K2S2O8-mediated regio- And stereo-selective thiocyanation of enamides with NH4SCN
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A direct and straightforward thiocyanation of enamides with NH4SCN under metal-free conditions has been accomplished. A variety of (E)-β-thiocyanoenamides are readily produced in a regio- and stereo-selective manner. The protocol features mild reaction conditions, good functional group tolerance and operational simplicity. The potential utility of this strategy was further demonstrated by transformation of thiocyanate into thiotetrazole-containing compounds and a Pd-catalyzed cross-coupling reaction to afford six- or seven-membered sulfur-containing heterocycles. Mechanistic insights into the reaction indicate that the reaction may proceedviaa radical mechanism.
- Gu, Qingyun,Wang, Qiyang,Dai, Wenjing,Wang, Xin,Ban, Yingguo,Liu, Tianqing,Zhao, Yu,Zhang, Yanan,Ling, Yong,Zeng, Xiaobao
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Read Online
- Boron-doped TiO2(B-TiO2): visible-light photocatalytic difunctionalization of alkenes and alkynes
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Boron-doped TiO2(B-TiO2) was prepared, characterized, and successfully applied as a reusable, inexpensive, available, and heterogeneous nanophotocatalyst under visible light for a novel method of construction of phenacyl thiocyanate compounds from double or triple bonds. Impressive aspects of this project are obtaining the desired compounds in a short time, using a renewable energy source, and using a catalyst with easy extraction that is solvent-safe, and without the use of any oxidants, bases, and ligands, or harsh conditions. This is the first report of the construction of phenacyl thiocyanates through this photocatalytic method under visible light.
- Hosseini-Sarvari, Mona,Valikhani, Atefe
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supporting information
p. 12464 - 12470
(2021/07/25)
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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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- α-Selective C(sp3)-H Thio/Selenocyanation of Ketones with Elemental Chalcogen
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A facile method is disclosed for the synthesis of α-thio/selenocyanato ketones through regioselective C-H thio/selenocyanation of ketones. The advantages include the use of easily available starting materials, high efficiency, simple operation, and easy scale-up. Control experiments provide evidence that the reaction proceeded via a radical way, while kinetic isotope effect experiments reveal that the cleavage of the C-H bond serves as the rate-limiting step.
- Li, Jin-Cheng,Gao, Wen-Xia,Liu, Miao-Chang,Zhou, Yun-Bing,Wu, Hua-Yue
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p. 17294 - 17306
(2021/12/02)
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- Visible-Light-Mediated Additive-Free Decarboxylative Ketonization Reaction of Acrylic Acids: An Access to α-Thiocyanate Ketones
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Visible-light-mediated additive-free decarboxylative functionalization of acrylic acids has been developed. The reaction uses inexpensive organic dye 9,10-dicyanoanthracene as a photocatalyst and uses the ubiquitous dioxygen as both an oxygen source and an oxidant. Through this mild and environmentally friendly method, a series of important α-thiocyanate ketones can be generated from easily available acrylic acids and ammonium thiocyanate. In addition, the facile transformation of product α-thiocyanate ketones makes this method have great potential for application in organic and pharmaceutical chemistry.
- Wang, Zhi-Lv,Chen, Jie,He, Yan-Hong,Guan, Zhi
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p. 3741 - 3749
(2021/03/09)
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- Photo-sensitized oxy-thiocyanation of terminal alkynes/1,3-aryldienes and their one-pot conversion to 2-hydroxy 4-substituted aryl thiazoles
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A regioselective visible light induced synthesis of aryl α-thiocyano ketones/thiocyano alcohols from activated terminal aryl alkynes and aryl 1,3-conjugated dienes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air in the presence of an organic photo-catalyst and NH4SCN. This protocol was also demonstrated at the 5 mmol scale for the synthesis of potentially therapeutic 2-hydroxy 4-substituted arylthiazoles in good yields, signifying its amenability for large-scale application.
- Gullapalli, Kumaraswamy,Vijaykumar, Swargam
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p. 2232 - 2241
(2019/02/27)
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- Visible-Light-Promoted Difunctionalization of Olefins Leading to α-Thiocyanato Ketones
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A simple and convenient visible-light-induced difunctionalization of alkenes with ammonium thiocyanate and dioxygen has been developed at room temperature. A series of α-thiocyanato ketones could be easily and efficiently obtained in moderate to good yields through the formation of C-S and C=O bonds simply by using nontoxic and inexpensive Na 2 -Eosin Y as a photocatalyst.
- Nan, Guangming,Yue, Huilan
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supporting information
p. 1340 - 1345
(2018/05/03)
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- One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)
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An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.
- Xu, Lijun,Wang, Hongyu,Zheng, Changwu,Zhao, Gang
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supporting information
p. 6057 - 6066
(2017/09/23)
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- A 2-thiocyano HYPNONE derivatives method for the preparation of
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The invention discloses a method for preparing 2-sulfur cyano acetophenone derivatives. The method for preparing the 2-sulfur cyano acetophenone derivatives comprises the following steps: dissolving styrene derivatives and ammonium thiocyanate in a solvent, and reacting at 20-30 DEG C to obtain 2-sulfur cyano acetophenone derivatives. According to the method for preparing the 2-sulfur cyano acetophenone derivatives, the styrene derivatives are taken as starting materials; the raw materials are easily available and various in type; products prepared by the method have various in type, can be directly used and can also be used for other further reactions; meanwhile, the method is mild in reaction conditions and simple in reaction operation and post-processing process; an accelerant does not need to be added; the production process meets the green and chemical requirements, is relatively high in yield and is suitable for large-scale production.
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Paragraph 0044-0047
(2016/10/10)
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- Molecular oxygen induced free radical oxythiocyanation of styrenes leading to α-oxothiocyanates
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A facile and efficient protocol of oxythiocyanation of styrenes with ammonium thiocyanate has been developed. The reaction proceeded at room temperature using oxygen as sole oxidant to afford the α-oxothiocyanates via radical pathway in moderate to good yields. This method is straightforward, green and cost-effective, requires no catalyst and additives.
- Liu, Kui,Li, Da-Peng,Zhou, Shao-Fang,Pan, Xiang-Qiang,Shoberu, Adedamola,Zou, Jian-Ping
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supporting information
p. 4031 - 4034
(2015/06/02)
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- Synthesis of ionic liquid-supported hypervalent iodine reagent and its application as a 'catch and release' reagent for α-substituted acetophenones
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A novel imidazolium-based ionic liquid-supported hypervalent iodine reagent has been synthesized and employed for a 'catch and release' strategy with substituted acetophenones to generate various α-substituted acetophenones in good to excellent yields. The use of an ionic liquid-supported hypervalent iodine reagent avoids chromatographic separation for the purification of α-substituted acetophenones and thus makes the method greener.
- Muthyala, Manoj Kumar,Choudhary, Sunita,Kumar, Anil
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p. 14297 - 14303
(2014/04/17)
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- Efficient α-thiocyanation of ketones using pyridinium hydrobromide perbromide
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The direct α-thiocyanation of ketones with ammonium thiocyanate has been achieved using pyridinium hydrobromide perbromide under mild and neutral conditions to produce α-ketothiocyanates in excellent yields and with high selectivity. Copyright
- Wu, Liqiang,Yang, Xiaojuan
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experimental part
p. 748 - 753
(2012/06/18)
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- Selectfluor: A novel and efficient reagent for the rapid α-thiocyanation of ketones
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The direct α-thiocyanation of ketones with ammonium thiocyanate has been achieved using Selectfluor under mild and neutral conditions to produce α-ketothiocyanates, in excellent yields and with high selectivity.
- Wu, Dezhen,Yang, Xiaojuan,Wu, Liqiang
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p. 901 - 905,5
(2020/09/09)
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- Cis-1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate as an efficient reagent for the synthesis of phenacyl thiocyanates and phenacyl azides
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Styrenes efficiently undergo thiocyanation and azidation with cis-1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate at 0C to furnish the corresponding thiocyanatoketones and azidoketones. This method is a direct, one-pot synthesis under mild condition using methanol as solvent.
- Badri, Rashid,Gorjizadeh, Maryam
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experimental part
p. 2058 - 2066
(2012/06/04)
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- A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate
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A very rapid, convenient, and general method for the synthesis of α-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl α-halo carbonyls, β-keto tosylates, α-halo β-dicarbonyl, α-tosyl, β-dicarbonyl, alkyl halide, and alkyl tosylates.
- Meshram,Thakur, Pramod B.,Madhu Babu,Bangade, Vikas M.
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experimental part
p. 1780 - 1785
(2012/05/04)
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- I2O5 as a mild, inexpensive, and environmentally benign oxidant for the α-thiocyanation of ketones
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-Thiocyanation of various ketones has been achieved using ammonium thiocyanate as a thiocyanation reagent and I2O5 as an oxidant in methanol solution at room temperature. Figure Presented.
- Wu, Liqiang,Yang, Xiaojuan,Yan, Fulin
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experimental part
p. 105 - 110
(2012/01/06)
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- Mild and efficient method for-thiocyanation of ketones and-dicarbonyl compounds using bromodimethylsulfonium bromide-ammonium thiocyanate
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An efficient and convenient method for-thiocyanation of ketones and-dicarbonyl compounds has been developed using a reagent combination of bromodimethylsulfonium bromide (BDMS) and ammonium thiocyanate in acetonitrile. The developed method is mild and gave good yield of the products at room temperature.
- Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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experimental part
p. 799 - 807
(2010/05/17)
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- Hypervalent iodine(III) sulfonate mediated synthesis of α-thiocynanatoketones in a task-specific ionic liquid [bmim]SCN
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The task-specific ionic liquid (TSIL) and 1-n-butyl-3-methylimidazolium thiocynanate, ([bmim]SCN) were used as the medium as well as the reactant for the synthesis of α-thiocynanatoketones by the reaction with α-sulfonyloxy aryl ketones. Significant rate enhancements and improved yields have been observed.
- Huang, Hsin-Yu,Wang, Huey-Min,Hou, Rei-Sheu,Cheng, Hui-Ting,Chen, Ling-Ching
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experimental part
p. 1204 - 1207
(2009/12/03)
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- Oxone as a mild, inexpensive, and environmentally benign oxidant for the α-thiocyanation of ketones
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An efficient and direct approach for the α-thiocyanation of ketones with α-hydrogens has been developed using ammonium thiocyanate as a thiocyanating agent and oxone as an oxidant in methanol. Copyright Taylor & Francis Group, LLC.
- Anil Kumar,Reddy, K. R. Kishore Kumar,Reddy, M. Veeranarayana,Reddy, C. Suresh,Reddy, C. Devendranath
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p. 2089 - 2095
(2008/09/21)
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- A novel and efficient method for the synthesis of α-azidoketones and α-ketothiocyanates
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α-Diazoketones underwent insertion smoothly with sodium azide and potassium thiocyanate in the presence of CeCl3 ·7H 2O under mild reaction conditions to afford the corresponding α-azidoketones and α-ketothiocyanates in excellent yields.
- Yadav,Subba Reddy,Srinivas
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p. 882 - 883
(2007/10/03)
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- Cerium(IV) ammonium nitrate mediated addition of thiocyanate and azide to styrenes: Expeditious routes to phenacyl thiocyanates and phenacyl azides
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An efficient synthesis of phenacyl thiocyanates and phenacyl azides is described here. Styrenes react with ammonium thiocyanate and sodium azide in the presence of cerium(IV) ammonium nitrate under an oxygen atmosphere to afford phenacyl thiocyanates and phenacyl azides respectively in good yields. (C) 2000 Published by Elsevier Science Ltd.
- Nair, Vijay,Nair, Latha G,George, Tesmol G,Augustine, Anu
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p. 7607 - 7611
(2007/10/03)
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- Synthesis of Pyrazoles and Fused Pyrazoles. Novel Synthesis of Pyrano[2,3-c]pyrazole, Thieno[2,3-c]pyrazole and Pyrazolo[3,4-b]pyridine Derivatives
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3-Methyl-1-thiocarbamoylpyrazol-5-one (1) reacted with p-methylphenacyl bromide to give 3-methyl-1-(4-p-tolylthiazol-2-yl)pyrazol-5-one (2). Compounds 1 and 2 were reacted with reagents such as α-cyanocinnamonitrile, benzaldehyde, elemental sulphur/malono
- Ibrahim,Elghandour,Abdel-Sayed,Abdel Fattah
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p. 206 - 208
(2007/10/03)
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