- 1-Aryltriazenes in the Suzuki, Heck, and Sonogashira Reactions in Imidazolium-ILs, with [BMIM(SO3H)][OTf] or Sc(OTf)3 as Promoter, and Pd(OAc)2 or NiCl2·glyme as Catalyst
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1-Aryltriazenes, the protected and more stable form of aryl-diazonium species, can be conveniently unmasked with Br?nsted acidic-IL or Sc(OTf)3 and coupled with a host of aryl/heteroaryl boronic acids, styrenes, and aryl/alkyl acetylenes in the Suzuki, Heck and Sonogashira reactions in one-pot and in respectable isolated yields, by using palladium or nickel catalyst in readily available imidazolium ILs as solvent, under mild conditions. The scope of these reactions are explored, and the potential for recovery/reuse of the IL solvent is also addressed.
- Sutar, Suraj M.,Savanur, Hemantkumar M.,Malunavar, Shruti S.,Prabhala, Pavankumar,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
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supporting information
p. 6088 - 6093
(2019/09/17)
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- COMPOUND, COMPOSITION COMPRISING THE SAME AND PAINT
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Provided are a compound represented by chemical formula 1, a composition comprising the same and a paint comprising the composition. In chemical formula 1, each substituent is the same as defined in the specification. The compound of the present invention, as a low temperature curable initiator, can form radicals at a low temperature, helps low temperature polymerization of an acrylic binder resin and performs low temperature curing, thereby providing a paint used in a low temperature curing type coating process.COPYRIGHT KIPO 2020
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Paragraph 0134; 0136-0137; 0145-0149
(2019/10/29)
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- One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides
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A simple and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure is based on the reaction of Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable the regioselective formation of triazenes via an intramolecular cyclization step. The new method can be used for the preparation of aryl, heteroaryl, vinyl, and alkyl triazenes. The synthetic utility of vinyl triazenes is demonstrated by acid-induced C-N, C-O, C-F, C-P, and C-S bond-forming reactions.
- Suleymanov, Abdusalom A.,Scopelliti, Rosario,Fadaei Tirani, Farzaneh,Severin, Kay
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supporting information
p. 3323 - 3326
(2018/06/11)
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- Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions
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An efficient, mild, and metal-free approach to direct diazenylation of N-heterocyclic compounds with aryltriazenes using Br?nsted ionic liquid as a promoter has been developed for the first time. Many N-heterocyclic azo compounds were synthesized in good to excellent yields at room temperature under an open atmosphere. Notably, the promoter 1,3-bis(4-sulfobutyl)-1H-imidazol-3-ium hydrogen sulfate could be conveniently recycled and reused with the same efficacies for at least four cycles.
- Cao, Dawei,Zhang, Yonghong,Liu, Chenjiang,Wang, Bin,Sun, Yadong,Abdukadera, Ablimit,Hu, Haiyan,Liu, Qiang
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supporting information
p. 2000 - 2003
(2016/06/01)
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- Sulfide synthesis through copper-catalyzed C-S bond formation under biomolecule-compatible conditions
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We report here an efficient and mild method for constructing C-S bonds. The reactions were carried out with Na2S2O3 as a sulfurating reagent, CuSO4 as a catalyst, and water as solvent without any surfactant. The products were achieved in moderate to excellent yields at room temperature under air. Notably, this reaction is compatible with various biomolecules including amino acids, oligosaccharides, nucleosides, proteins, and cell lysates. This journal is
- Zhang, Yonghong,Li, Yiming,Zhang, Xiaomei,Jiang, Xuefeng
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supporting information
p. 941 - 944
(2015/01/09)
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- N2 extrusion and co insertion: A novel palladium-catalyzed carbonylative transformation of aryltriazenes
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A novel procedure for the replacement of N2 with CO of aryltriazenes has been developed. Aryltriazenes were converted to the corresponding arylamides catalyzed by 1 mol % of PdCl2/P(o-Tol)3 under CO pressure. In this process, aryldiazonium salts were generated in the presence of 40 mol % of MeSO3H. Nitrogen was released from the substrates and CO formally inserted. Aryl bromides, iodides, alkynes, and free hydroxyl groups can be tolerated in this transformation.
- Li, Wanfang,Wu, Xiao-Feng
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supporting information
p. 1910 - 1913
(2015/04/27)
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- Palladium-catalyzed carbonylative Sonogashira coupling between aryl triazenes and alkynes
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We developed a palladium-catalyzed carbonylative Sonogashira reaction with aryl triazenes and alkynes as substrates and methanesulfonic acid as the additive. A series of α,β-ynones were synthesized by this alternative procedure. Notably, bromides, iodides
- Li, Wanfang,Wu, Xiao-Feng
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supporting information
p. 5090 - 5093
(2015/05/13)
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- Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source
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Various sulfonamides have been synthesized from triazenes and sulfur dioxide. In the presence of just a catalytic amount of BF3· OEt2, a series of 1-aryl-triazenes were converted into sulfonyl hydrazines in good to excellent yields. When using CuCl2 as the catalyst, the corresponding sulfonamides can be produced from the 1-aryl triazenes in good yields. This journal is the Partner Organisations 2014.
- Li, Wanfang,Beller, Matthias,Wu, Xiao-Feng
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supporting information
p. 9513 - 9516
(2014/08/18)
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- General and efficient synthesis of indoles through triazene-directed c-h annulation
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Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered N-N bond cleavage. It allows rapid conversion of the reaction products into several functional molecules. Copyright
- Wang, Chengming,Sun, Huan,Fang, Yan,Huang, Yong
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supporting information
p. 5795 - 5798
(2013/06/27)
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- Ligand-free Suzuki-Miyaura cross-coupling reactions of aryltriazenes with arylboronic acids
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The boron trifluoride induced Suzuki-Miyaura cross-coupling of aryltriazenes with arylboronic acids catalyzed by Pd(OAc)2 without added ligands has been achieved for the first time. The reactions performed at room temperature under an argon atmosphere give biaryls in good to excellent yields. It is noteworthy that the reactions were conducted under mild and ligand-free conditions. The boron trifluoride induced Suzuki-Miyaura cross-coupling of aryltriazenes with arylboronic acids catalyzed by Pd(OAc) 2 without added ligands has been achieved for the first time. Copyright
- Nan, Guangming,Zhu, Fanghua,Wei, Zhijun
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experimental part
p. 72 - 78
(2012/03/27)
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- Thermal cis-to-trans isomerisation of triazene dyes in doped polymer films
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The kinetics of the thermal conversion of the cis to the trans isomeric forms of 1,3-diphenyltriazene and 1-phenyltriazenes derived from cyclic amines were determined in both poly(methyl methacrylate) and polystyrene doped films in the glassy state, using
- Tabone, Ryan,Barra, Mónica
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experimental part
p. 180 - 186
(2011/01/12)
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- Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-palladium complex catalyst
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The Suzuki-Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported Pd-NHC complex catalyst has been realized for the first time. The polymer-supported catalyst can be re-used several times still retaining high activity for this transformation. Various aryltriazenes were investigated as electrophilic substrates at room temperature to give biaryls in good to excellent yields and showed good chemoselectivity over aryl halides in the reactions.
- Nan, Guangming,Ren, Fang,Luo, Meiming
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experimental part
(2010/11/21)
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- Effect of medium on acid-catalyzed decomposition of N-(phenylazo)-substituted nitrogen heterocycles
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Four N-(phenylazo)-substituted saturated nitrogen heterocyclics were synthesized and their structure was confirmed by 1H and 13C NMR spectroscopy. The kinetics of their acid-catalyzed decomposition were studied at various concentrations of the catalyst (pivalic acid) in 40, 30, and 20% (v/v) aqueous ethanol at 25 °C. The values obtained for the observed rate constants were processed by the non-linear regression method according to the suggested kinetic models and by the method of principal component analysis (PCA). The interpretation of the results has shown that the acid-catalyzed decomposition of the heterocyclics under the conditions used proceeds by the mechanism of general acid catalysis, the proton being the dominant catalyst particle of the rate-limiting step. The decrease in the observed rate constant at higher concentrations of the catalyst was explained by the formation of a non-reactive complex composed of the undissociated acid and the respective N-(phenylazo)hetcrocycle. The effect of medium and steric effect of the heterocyclic moiety on the values of catalytic rate constant are discussed.
- Ludwig, Miroslav,Bednarova, Iva,Parik, Patrik
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p. 1654 - 1672
(2007/10/03)
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