Cu(I)-Catalyzed Macrocyclic Sonogashira-Type Cross-Coupling

Abstract

A macrocyclic Cu-catalyzed Sonogashira-type cross-coupling reaction has been developed that employs an operationally simple CuCl/phen/Cs2CO3 catalyst system. Macrocyclizations can be performed at relatively high concentrations without the need for slow addition techniques and form macrocycles with various ring sizes and functional groups. The optimized protocol was employed in the synthesis of (S)-zearalane, demonstrating applicability toward the synthesis of a macrocycle with known biological activity.

A highly efficient nano-sized Cu2O/SiO2egg-shell catalyst for C–C coupling reactions

“…33,34 In this type of reaction, Cu 2 O nanoparticles activate phenylacetylene to form copper(I) acetylide compounds, which subsequently react with acyl chloride. 35,36 In addition, this reaction does not require any ligand and palladium source under solvent-free conditions.…”

An Eosin Y Encapsulated Cu(I) Covalent Metal Organic Framework for Efficient Photocatalytic Sonogashira Cross-coupling Reaction

“…Conventionally, noble metals, such as palladium(Pd) complexes and Pd/Cu composites are used to thermally catalyze Sonogashira cross-coupling reaction [15][16][17] . On the other hand, great efforts have been made to investigate the Sonogashira cross-coupling reactions catalyzed by non-precious metal, such as Fe, Ni, and Cu, instead of the high cost noble metal [18,19] . However, these catalytic reactions rarely work under mild condition, such as at room temperature(r.t.) and most of them undergo under harsh condition, such as high temperature and strong base [17] .…”

A novel and highly efficient polyaniline‐functionalized multiwall carbon nanotube‐supported cu(I) complex for Sonogashira coupling reactions of aryl halides with phenylacetylene

“…Recently, much effort has been devoted to the employment of copper complexes as catalysts for the Sonogashira coupling of aryl halides with terminal alkynes, because copper salts are relatively economical and the system is mild and simple. In recent years numerous copper‐based catalytic systems have been reported, including, Cu(I)/diamine, the salt of [ N ‐benzyl DABCO] + [Cu 4 Cl 5 ] − , choline chloride/CuCl, monobenzylnicotinium chloride combined with copper(I) chloride, Cu 2 O/tetraethylammonium prolinate, CuCl/Phen/Cs 2 CO 3 , CuI/1,10‐phenanthroline and CuI/2,2‐bipyridine, Cu 2 Se nanoflakes and DABCO‐functionalized silica‐supported copper(I) complex . Hence, the development of a novel catalytic system that is efficient, readily available, inexpensive, eco‐friendly and operative under mild conditions would be useful in contemporary synthesis.…”