Modern Development in Copper‐ and Nickel‐Catalyzed Cross‐Coupling Reactions: Formation of Carbon‐Carbon and Carbon‐Heteroatom bonds under Microwave Irradiation Conditions

Abstract

The use of transition metals in cross‐coupling reactions has been verified as a powerful tool in synthetic organic chemistry to access valuable pharmaceutical intermediates and functional organic molecules. Copper compounds were described for building a variety of Carbon‐Carbon and Carbon‐Heteroatom bonds more than a century ago. Whereas nickel‐catalyzed cross‐coupling was emerged in the 1972. The general reactivity of the reaction conversion was enhanced during the last two decades, particularly under microwave irradiation conditions. The focus of this review article accentuates the recent development and sustainable achievement of copper‐ and nickel‐catalyzed cross‐coupling of different electrophiles and nucleophiles or two sort of nucleophiles under microwave irradiation conditions. The published cross‐coupling protocols during the last ten years were critically reviewed, this includes the type and amount of metal catalyst used, solventless and ligandless conditions and the application in the synthesis of complex heterocycles. Furthermore, various proposed reaction mechanisms covering radical path or through the involvement of metal complexes in different oxidation states were highlighted and discussed.

Advances in Cross-Coupling Reactions Catalyzed by Aromatic Pincer Complexes Based on Earth-Abundant 3d Metals (Mn, Fe, Co, Ni, Cu)

“…Carbon-carbon cross-coupling reactions have emerged as one of the most powerful tools for constructing complex organic molecules [41]. These reactions have revolutionized the field of organic synthesis by providing a versatile and efficient method for the formation of C-C bonds [42].…”

New sustainable and robust catalytic supports for palladium nanoparticles generated from chitosan/cellulose film and corn stem biochar

“…Typical catalytic systems for cross-coupling reactions employ a metallic catalyst (Pd normally), auxiliary ligand to stabilize the metal, Lewis base to neutralize the system, solvent, inert atmosphere, and heating (Diederich and Meijere 2004 ; Negishi 2002 ). Efforts have been reported in order to reduce the amount of catalytically active species in reactions (Roy and Uozumi 2018 ) or replace it with a more eco-friendly and less expensive metal (Ma et al 2021 ); reduce the use of auxiliary ligands (Serrano et al 2022 ); employ less toxic solvents (Su et al 2022 ) and bases (Long et al 2019 ); and make the reaction conditions milder through the use of lower temperatures (close to room temperature) (Ma et al 2022 ), microwave heating (Salih 2022 ), sonication (Wilson et al 2018 ), or elimination of the inert atmosphere (Tian et al 2022 ). In addition, the search for new, greener catalytic systems employing biomass sources appears frequently in literature, such as in the use of biomass extracts to prepare metal nanoparticles (NPs) via biogenic routes (Schmitt et al 2021 ) or green solvents applied in carbon–carbon and carbon–heteroatom couplings (Peixoto et al 2022 ).…”