Green carbon–carbon homocoupling of terminal alkynes by a silica supported Cu(<scp>ii</scp>)-hydrazone coordination compound

Heydari, Neda; Bikas, Rahman; Siczek, Miłosz; Lis, Tadeusz

doi:10.1039/d2dt03054c

Cited by 21 publications

(1 citation statement)

References 124 publications

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“…Heterogeneous catalysis has also been used for this aim. For example, copper hydroxide on TiO 2 [54], cuprous chloride-doped zeolites [55][56][57], silica-supported Cu(II)-hydrazone coordination compounds [58], Cu 3 (BTC) 2 metal organic framework [59] and even naturally occurring copper-containing minerals, chalcocite (Cu 2 S) and bornite (Cu 5 FeS 4 ) [60], have demonstrated high efficiency as catalysts for terminal alkyne coupling. The reaction was also performed in supercritical fluids [61,62], water [63,64], ionic liquids [65,66] and solvent-free conditions [67,68] and under photocatalysis [69].…”

Section: Introductionmentioning

confidence: 99%

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

Muzalevskiy,

Shastin,

Tirkasheva

et al. 2023

Catalysts

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A novel catalytic system for homocoupling terminal acetylenes was elaborated based on CuCl as a catalyst (10 mol%), TMEDA as a base and CCl4 as an oxidant. The influence of the solvent, base, amount of catalyst and CCl4 on the reaction was investigated. Methanol was found to be the solvent of choice. The broad synthetic scope of the reaction was demonstrated. Diynes with various substituents were prepared in up to 92% yields. The possible reaction mechanism is discussed.

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Section: Introductionmentioning

confidence: 99%

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

Muzalevskiy,

Shastin,

Tirkasheva

et al. 2023

Catalysts

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Integrating Sustainable Chemistry Principles in Polydiacetylene (PDA) Synthesis

Gendron,

Baillargeon

2024

Asian J Org Chem

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Polydiacetylenes (PDAs) represent one of the most intriguing classes of semiconducting polymers, captivating researchers with their unique properties and diverse applications. They possess remarkable electronic and optical characteristics, as well as their ability to undergo dramatic color changes in response to various stimuli. This perspective explores the integration of sustainable chemistry principles into the synthesis of PDAs. We highlight how several elements such as diacetylene green‐coupling synthesis, biodegradability, solid state synthesis and biobased precursors, can contribute to the advancement of more responsible and innovative PDAs materials.

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Synthesis, structure, and catalytic performance of solvent induced zinc clusters in furan synthesis by cycloisomerization reaction

Farzaneh‐Bonab,

Bikas,

Noshiranzadeh

et al. 2024

Applied Organom Chemis

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Two Zn(II) clusters were synthesized by the reaction of Zn(OAc)2·2H2O and 1,2‐bis(2‐hydroxy‐3‐methoxybenzylidene)hydrazine as a N2O4‐donor Schiff base ligand in 1:3 molar ratio. The reaction in methanol gave yellow‐brown needle crystals, while block yellow crystals were achieved in a mixture of methanol:water (50:50 v/v). Investigation of the crystals by single crystal X‐ray analysis showed that solvent has considerable effect on the structure and composition of the products. In methanol, two independent pentanuclear Zn(II) clusters with the same general formula of [Zn5(L)2(μ‐OAc)4(OAc)2(CH3OH)2] but different coordination environments around Zn(II) cores, and bridging mode of the acetate ligands are present in the unit cell. In a mixture of methanol:water, a pentanuclear cluster and a 1D coordination polymer with pentanuclear repetitive unit are simultaneously present in the crystal structure. These compounds were further characterized by spectroscopic techniques, and they were used as catalysts for intramolecular cycloisomerization of 1,4‐diphenylbut‐3‐yn‐1‐one. The results indicated that these Zn(II) clusters can efficiently produce 2,5‐diphenylfuran through catalytic cycloisomerization reaction.

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Green carbon–carbon homocoupling of terminal alkynes by a silica supported Cu(ii)-hydrazone coordination compound

Abstract: Cu(II) complex, [Cu(HL)(NO3)(CH3OH)]∙CH3OH (1), was obtained by the reaction of Cu(NO3)2∙3H2O and H2L in methanol solvent (H2L is (E)-4-amino-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide). H2L and compound 1 were characterized by various spectroscopic analyses and...

Cited by 21 publications

References 124 publications

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

CCl4-TMEDA-CuCl—A Novel Convenient Catalytic System for Dimerization of Terminal Acetylenes in Mild Conditions

Integrating Sustainable Chemistry Principles in Polydiacetylene (PDA) Synthesis

Synthesis, structure, and catalytic performance of solvent induced zinc clusters in furan synthesis by cycloisomerization reaction

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