Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate

Hajipour, Abdol R.; Mohammadsaleh, Fatemeh

doi:10.1016/j.tetlet.2014.10.045

Cited by 15 publications

(13 citation statements)

References 29 publications

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“…In the final step, the aryl azide is released via a reductive elimination step and released the catalyst for the next catalytic run. [47] 2 CuI/L-proline 5 93 [43] 3 Cu/L-proline/Base 24 96 [45] 4 CuFeO 2 /L-proline/Base 10 96 [53]…”

Section: Investigation Of Catalytic Activity Of [Cu (Ii)(btp)(otf) mentioning

confidence: 99%

“…Completion of the reaction needed a higher reaction temperature in which the aryl azides were decomposed . Recently, Cu 2 O/tetraethylammonium prolinate and Proline/CuFeO 2 have been reported for conversion of aryl halides to aryl azides …”

Section: Introductionmentioning

confidence: 99%

“…[24,46] Recently, Cu 2 O/tetraethylammonium prolinate and Proline/CuFeO 2 have been reported for conversion of aryl halides to aryl azides. [45,47] According to the above mentioned points and by considering the potential application of organic azides, herein, we introduce the synthesis of aryl azides by the reaction of aryl halides with sodium azide in the polyethylene glycol 400 (PEG-400) as solvent catalyzed by chloromethylated polystyrene supported Cu (II) bis-thiazole complex (Scheme 1).…”

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confidence: 99%

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Chloromethylated polystyrene supported copper (II) bis–thiazole complex: Preparation, characterization and its application as a heterogeneous catalyst for chemoselective and homoselective synthesis of aryl azides

Dehbanipour

Tangestaninejad

Mirkhani

et al. 2018

Applied Organom Chemis

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This work deals the synthesis of aryl azides catalyzed by heterogeneous copper (II) complex of 3,5–bis (2–benzothiazolyl) pyridine, [Cu (II)(BTP)(OTf)2], immobilized on chloromethylated polystyrene, [Cu (II)(BTP)(OTf)2]@CMP. The prepared catalyst was characterized by different analytical techniques such as X‐ray diffraction (XRD), thermogravimetric analysis (TGA), field emission scanning electron microscopy (SEM), energy dispersive X–ray spectroscopy (EDX), elemental analysis, and FT‐IR and UV–Vis spectroscopic methods. This catalytic system showed excellent activity in the synthesis of aryl azides by the reaction of aryl halides with sodium azide in the presence of catalytic amounts of [Cu (II)(BTP)(OTf)2]@CMP. Moreover, this unique catalyst could be recovered easily and reused several times without any considerable loss of its catalytic activity.

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Section: Investigation Of Catalytic Activity Of [Cu (Ii)(btp)(otf) mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Chloromethylated polystyrene supported copper (II) bis–thiazole complex: Preparation, characterization and its application as a heterogeneous catalyst for chemoselective and homoselective synthesis of aryl azides

Dehbanipour

Tangestaninejad

Mirkhani

et al. 2018

Applied Organom Chemis

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“…In continuation of our recent studies on the design of catalytic systems containing amino acids, and as a part of our goal to develop copper‐based catalysts for Sonogashira coupling reactions, in the work reported herein we evaluated the actions of several combinations of CuI/amino acids in Sonogashira coupling reactions (Scheme ). Between the different tested amino acids (phenylalanine, methionine and proline), methionine showed the best results.…”

Section: Introductionmentioning

confidence: 99%

Methionine: a green and efficient promoter for copper‐catalyzed Sonogashira cross‐coupling reactions

Hajipour

Mohammadsaleh

2015

Applied Organom Chemis

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aIn the presence of amino acids as environmentally friendly ligands, CuI-catalyzed Sonogashira cross-coupling of various aryl halides with phenylacetylene was conducted to afford the corresponding internal alkynes. L-Methionine was found to be useful for this palladium-free and amine-free coupling reaction. It was also found that the solvent system plays an important role in this reaction, and significantly affects the product formation and reaction rate. Sonogashira coupling of aryl iodides and aryl bromides in dimethylsulfoxide or dimethylformamide gave the coupled products in good to excellent yields.

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“…Iodobenzene was also tested as a possible substrate in our attempts to generate the relevant aryl triazole analogues, however these efforts were unsuccessful. This was not surprising as the azidonation of aryl halides 21,69,70 is generally a slow process that requires very harsh or tedious conditions. We therefore employed the inexpensive and readily available benzeneboronic acid in order to obtain the corresponding product 71 .…”

Section: Esi-msmentioning

confidence: 99%

Copper(ii)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study

et al. 2018

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This diagnostic study aims to shed light on the catalytic activity of a library of Cu(ii) based coordination compounds with benzotriazole-based ligands. We report herein the synthesis and characterization of five new coordination compounds formulated as [Cu(L)(MeCN)(CFSO)] (1), [Cu(L)(CFSO)] (2), [Cu(L)(MeCN)(CFSO)]·(CFSO) (3), [Cu(L)(HO)(CFSO)]·(CFSO)·2(MeCO) (4), and [Cu(L)(L)(CFSO)]·4(CFSO)·8(MeCO) (5), derived from similar nitrogen-based ligands. The homogeneous catalytic activity of these compounds along with our previously reported coordination compounds (6-13), derived from similar ligands, is tested against the well-known Cu(i)-catalysed azide-alkyne cycloaddition reaction. The optimal catalyst [Cu(L)(CFSO)] (10) activates the reaction to afford 1,4-disubstituted 1,2,3-triazoles with yields up to 98% and without requiring a reducing agent. Various control experiments are performed to optimize the method and examine parameters such as ligand variation, metal coordination geometry and environment, in order to elucidate the behaviour of the catalytic system.

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Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate

Cited by 15 publications

References 29 publications

Chloromethylated polystyrene supported copper (II) bis–thiazole complex: Preparation, characterization and its application as a heterogeneous catalyst for chemoselective and homoselective synthesis of aryl azides

Chloromethylated polystyrene supported copper (II) bis–thiazole complex: Preparation, characterization and its application as a heterogeneous catalyst for chemoselective and homoselective synthesis of aryl azides

Methionine: a green and efficient promoter for copper‐catalyzed Sonogashira cross‐coupling reactions

Copper(ii)-benzotriazole coordination compounds in click chemistry: a diagnostic reactivity study

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