Copper complexes of arylselenolate-based ligands: synthesis and catalytic activity in azide–alkyne cycloaddition reactions

Chauhan, Rohit Singh; Oza, Dhvani; Yadav, Seema; Dash, Chandrakanta; Slawin, Alexandra M. Z.; Shivran, Neelam

doi:10.1039/c8nj04602f

Cited by 15 publications

(17 citation statements)

References 58 publications

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“…Additional references cited within the Supporting Information. [59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77] All experimental procedures and data are described in the Supporting Information.…”

Section: Synthesis Of Cu-tazo-tapbmentioning

confidence: 99%

Imine‐Linked Porous Organic Polymer Gel and Immobilization of Copper(II): Easy Synthesis and Excellent Catalyst for Huisgen [3+2] Cycloaddition Reactions

Joseph

Kundu

2023

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Porous organic polymeric gels (POP gels) were made by condensation of a newly synthesized C3‐symmetrical azobenzene‐based tri‐salicylaldehyde building block, 1,3,5‐tris(4‐((3‐formyl‐4‐hydroxyphenyl)diazenyl)phenyl)benzene (TAzo) with suitable aromatic tri‐ and di‐amines in N,N‐dimethylformamide (DMF) at ambient conditions. Here, we have furnished the pathway of an efficient, gentle, and simple one‐pot synthesis of imine‐linked porous organic polymers at room temperature without any acid catalysts. Detail rheological properties of the POP‐gels were studied and were also found to be stable for at least a year at room temperature. Nitrogen isotherm revealed the mesoporous nature of the gel‐powders with moderate surface area. Iminophenol moieties are known to provide binding sites to metallic species via the strong coordination interaction with hydroxy (−OH) and imine (−HC=N−) groups. We have successfully synthesized a copper‐metallated POP by immobilizing copper ions in one of the POP‐gels. The mesoporous POP material having 3 wt % copper loading was utilized for the solvent‐free Huisgen [3+2] cycloaddition reactions of various aryl, benzyl, and alkyl azides with terminal alkynes containing aromatic, heteroaromatic, and alkyl groups with excellent yield. The heterogeneous catalyst with low catalyst loading (1 mol %) was highly regioselective towards 1,4‐disubstituted 1,2,3‐triazoles, recyclable, and did not require the addition of a reducing agent.

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Section: Synthesis Of Cu-tazo-tapbmentioning

confidence: 99%

Imine‐Linked Porous Organic Polymer Gel and Immobilization of Copper(II): Easy Synthesis and Excellent Catalyst for Huisgen [3+2] Cycloaddition Reactions

Joseph

Kundu

2023

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“…1 H NMR (500 MHz, CDCl 3 ): δ 8.15 (s, 1H), 7.92-7.90 (m, 2H), 7.67-7.66 (m, 2H), 7.47-7.44 (m, 2H), 7.38-7.31 (m, 3H), 2.43 (s, 3H) ppm. 13 C{ 1 H} NMR (125 MHz, CDCl 3 ): δ 148.4, 139.0, 134.9, 130.5, 130.3, 129.0, 128.4, 125.9, 120.5, 117.7, 21.2 ppm. [26] 0.203 g (2 a), 0.…”

Section: General Procedures For the Azide-alkyne Click Reactionmentioning

confidence: 99%

“…[11c] Our group reported a series of copper(II) complexes supported by arylselenolate-based ligands for azide-alkyne cycloaddition in water. [13] Thus, following our continuous interest in the development of well-defined transition metal based catalysts, herein, we report the synthesis, characterization, and catalytic activity of copper(II)-bis(imino)pyridine complexes, 2 a&2 b(Figure 1). The copper(II)-bis(imino)pyridine complexes efficiently catalyze azide-alkyne Click reactions for thesynthesis of 1,4disubstituted 1,2,3-triazoles.…”

Section: Introductionmentioning

confidence: 99%

Copper(II) Complexes Supported by Bis(imino)pyridine Ligands: Synthesis and Catalysis on Azide‐Alkyne Click Reactions

2023

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The synthesis, characterization and catalytic activity of copper(II)‐bis(imino)pyridine pincer complexes were described. The copper(II) complexes (2 a and 2 b) were synthesized by the reaction of 2,6‐bis(imino)pyridine ligands with CuCl2 ⋅ 2H2O in methanol as a solvent. The copper(II) complexes were fully characterized by IR, UV‐Visible, Mass spectroscopy and elemental analysis. The copper(II) complexes 2 a and 2 b showed excellent catalytic activity towards azide‐alkyne cycloaddition (Click reaction) in water and produced regioselective product of 1,4‐disubstituted‐1,2,3‐triazoles. The copper(II) complex (2 b) with electron withdrawing CF3 group exhibited comparatively higher catalytic activity in azide‐alkyne cycloaddition reactions and produced up to 93 % of yield with 0.05 mol % of the catalyst loading.

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“…In 2019, our group has reported the Cu II ‐catalyzed azide‐alkyne cycloaddition reaction in water [9] . As part of our research interest in our group for the development of transition metal based catalysts in heterocyclic synthesis, [10] we became interested to utilize the zinc(II)‐ bis (imino)pyridine complexes as catalysts in azide‐alkyne cycloaddition reactions.…”

Section: Introductionmentioning

confidence: 99%

“…[8] In 2019, our group has reported the Cu II -catalyzed azidealkyne cycloaddition reaction in water. [9] As part of our research interest in our group for the development of transition metal based catalysts in heterocyclic synthesis, [10] we became interested to utilize the zinc(II)-bis(imino)pyridine complexes as catalysts in azide-alkyne cycloaddition reactions. Azide-alkyne cycloaddition reaction catalyzed by zinc metal as catalyst was first reported by Chen et al [11] Greaney et al and Postnikov et al have also reported the zinc mediated azide-alkyne cycloaddition reactions.…”

Section: Introductionmentioning

confidence: 99%

Zinc‐bis(imino)pyridine Complexes as Catalysts for Azide‐Alkyne Cycloaddition in Water

et al. 2022

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Two new zinc(II) complexes, [2,6‐bis(methylphenyliminomethyl)pyridine]ZnBr2 (2 a) and [2,6‐bis(triflouromethylphenyliminomethyl)pyridine]ZnBr2 (2 b) were synthesized by the reactions of corresponding 2,6‐bis(imino)pyridine based [NNN]‐pincer ligand and anhydrous ZnBr2 in acetonitrile as a solvent. The catalytic properties of zinc(II) complexes were examined in azide‐alkyne cycloaddition reactions in water. The zinc(II) complexes were characterized by UV‐Vis, 1H NMR, IR, elemental analysis and mass spectroscopy. The zinc complex [2,6‐bis(triflouromethylphenyliminomethyl)pyridine]ZnBr2 was characterized by X‐ray crystallography. The zinc(II) complexes efficiently catalyzed the azide‐alkyne cycloaddition reaction for the synthesis of 1,2,3‐triazoles (mixture of 1,4‐ and 1,5‐disubstituted 1,2,3‐triazoles) in water with good to excellent yields.

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Copper complexes of arylselenolate-based ligands: synthesis and catalytic activity in azide–alkyne cycloaddition reactions

Abstract: Arylselenolate-based copper complexes have been synthesized and used as pre-catalysts for azide-alkyne cycloaddition reactions.

Cited by 15 publications

References 58 publications

Imine‐Linked Porous Organic Polymer Gel and Immobilization of Copper(II): Easy Synthesis and Excellent Catalyst for Huisgen [3+2] Cycloaddition Reactions

Imine‐Linked Porous Organic Polymer Gel and Immobilization of Copper(II): Easy Synthesis and Excellent Catalyst for Huisgen [3+2] Cycloaddition Reactions

Copper(II) Complexes Supported by Bis(imino)pyridine Ligands: Synthesis and Catalysis on Azide‐Alkyne Click Reactions

Zinc‐bis(imino)pyridine Complexes as Catalysts for Azide‐Alkyne Cycloaddition in Water

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