Copper(I) Oxide Catalyzed N-Arylation of Azoles and Amines with Arylboronic Acid at Room Temperature under Base-Free Conditions

Sreedhar, B.; Venkanna, Gopaladasu T.; Kumar, K. B. Shiva; Balasubrahmanyam, V.

doi:10.1055/s-2008-1032184

Cited by 64 publications

(22 citation statements)

References 2 publications

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“…The preparation of [4]helicene-2benzimidazolium iodide (1-(benzo[c]phenanthren-2yl)-3-methyl-1H-benzimidazol-3-ium iodide; 7) was then achieved in two steps. First, a Chan-Lam [36,37] coupling between the boronic acid 5 and benzimidazole, using Cu 2 O as the copper source in methanol open to the air, [38] yielded [4]helicene-2-benzimidazole (1-(benzo[c]phenanthren-2-yl)-1H-benzimidazole; 6) in 63 % yield. This compound was then N-methylated by treatment with an excess of methyl iodide, to give the imidazolium salt 7 in 85 % yield.…”

Section: Synthesis Of Cycloiridiated Complex C Bearing a [4]helicenicmentioning

confidence: 99%

An Enantiopure Cyclometallated Iridium Complex Displaying Long‐Lived Phosphorescence both in Solution and in the Solid State

Macé

Hellou

Hammoud

et al. 2019

Helvetica Chimica Acta

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A new enantiopure cyclometallated iridium complex bearing a [4]helicenic :C∧C- ‐coordinating and two :N∧C- ‐coordinating dfppy (2‐(2,4‐difluorophenyl)‐pyridyl) ligands was prepared. This complex displayed long‐lived phosphorescence both in solution and in the solid state. Its chiroptical properties, namely electronic circular dichroism and circularly polarized luminescence, were also examined. Comparison with former chiral complexes enabled assignment of the ΔIr‐(−) and ΛIr‐(+) absolute configurations.

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Section: Synthesis Of Cycloiridiated Complex C Bearing a [4]helicenicmentioning

confidence: 99%

An Enantiopure Cyclometallated Iridium Complex Displaying Long‐Lived Phosphorescence both in Solution and in the Solid State

Macé

Hellou

Hammoud

et al. 2019

Helvetica Chimica Acta

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“…[10] However, under our standard conditions here we did not detect the formation of a coupling product between pyrrolidine and p-nitrophenylboronic acid. In contrast, Chan-Lam coupling of aliphatic amines with aryl boronic acids using copper acetate [16] or copper oxide [17] gave good to excellent yields. In addition to coupling aryl boronic acids with imidazole we obtained the results of reaction conditions with the coupling of p-nitrophenyl and p-methoxyphenyl boronic acid with pyrazole, 1H-2,4-triazole, benzimidazole, and indole ( Table 4).…”

Section: Resultsmentioning

confidence: 84%

Copper(I) 3-Methylsalicylate Mediates the Chan–Lam N-Arylation of Heterocycles

Farahat

Boykin

2014

Synthetic Communications

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Copper(I) 3-methylsalicylate (CuMeSal) mediates N-arylation reactions between aryl boronic acids and aromatic heterocycles (Chan-Lam coupling) under moderate reaction conditions (K 2 CO 3 , methanol, 65 C, in air, 3-5 h). Both electron-rich and electrondeficient aryl boronic acids and a diverse set of N-heterocycles were allowed to react and gave N-arylation products in reasonable yields, which demonstrate the utility of this catalyst.

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“…Procedure for Chan-Lam coupling reaction using Cu/BNC catalyst N-benzylaniline (7) was obtained using amine (6) and Cu/BNC catalyst at room temperature [36]. Briefly, to a solution of amine 6 (17 mg, 0.16 mmol) in methanol (0.5 mL)…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

Jeremić

Djokić

Ajdačić

et al. 2019

International Journal of Biological Macromolecules

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Please cite this article as: S. Jeremic, L. Djokic, V. Ajdačić, et al., Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions, International Journal of Biological Macromolecules, https://doi. AbstractBacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability.BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L -1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 weight %, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4'fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction.Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.

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Copper(I) Oxide Catalyzed N-Arylation of Azoles and Amines with Arylboronic Acid at Room Temperature under Base-Free Conditions

Cited by 64 publications

References 2 publications

An Enantiopure Cyclometallated Iridium Complex Displaying Long‐Lived Phosphorescence both in Solution and in the Solid State

An Enantiopure Cyclometallated Iridium Complex Displaying Long‐Lived Phosphorescence both in Solution and in the Solid State

Copper(I) 3-Methylsalicylate Mediates the Chan–Lam N-Arylation of Heterocycles

Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

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