ZrO2 Supported Cu Nanoparticles for Sonogashira and Ullmann Coupling Reactions Under Palladium-Free Conditions

Cu nanoparticles supported on ZrO 2 (CuNPs@ZrO 2 ) were synthesized using a one‐step co-precipitation process, and their application in C–C coupling reactions was investigated. The catalyst was characterized using XRD, XPS, SEM, TEM, and TGA techniques. The prepared catalyst was used for the Sonogas...

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Bibliographic Details
Published in:Catalysis letters 2024-06, Vol.154 (6), p.3078-3090
Main Authors: Patil, Seema P., Rajmane, Archana S., Jadhav, Sanjay N., Rajmane, Vijaya S., Rode, Chandrashekhar V., Kumbhar, Arjun S.
Format: Article
Language:English
Subjects:
Acetylene
Alkynes
Aromatic compounds
Bromides
Catalysis
Catalysts
Chemical reactions
Chemistry
Chemistry and Materials Science
Copper
Cross coupling
Halides
Industrial Chemistry/Chemical Engineering
Inert atmospheres
Nanoparticles
Organometallic Chemistry
Palladium
Physical Chemistry
X ray photoelectron spectroscopy
Zirconium dioxide
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Summary:Cu nanoparticles supported on ZrO 2 (CuNPs@ZrO 2 ) were synthesized using a one‐step co-precipitation process, and their application in C–C coupling reactions was investigated. The catalyst was characterized using XRD, XPS, SEM, TEM, and TGA techniques. The prepared catalyst was used for the Sonogashira cross-coupling reactions of aryl bromides with phenyl-acetylene in the presence of K 2 CO 3 in DMF at 110 °C, which resulted in substituted alkynes with good to excellent yields. The protocol was also extended for the Ullmann coupling reactions of aryl iodides under similar reaction conditions, yielding the desired products with good to excellent yields without homo-coupling. Interestingly, unlike other copper catalysts, the present catalyst worked under air and did not require an inert atmosphere to prevent alkyne. This catalytic system is versatile, tolerant, and significantly cheaper than the “traditional” Pd-catalyzed Sonogashira cross-coupling of terminal alkynes with aryl halides. The catalyst could be reused for five catalytic cycles with no significant change in the product yield. All of these characteristics make our prepared CuNPs@ZrO 2 catalyst quite suitable for the gram-scale synthesis of biaryls and alkynes, with a simple workup. Graphical Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-023-04513-w