Copper(i) catalyzed Sonogashira reactions promoted by monobenzyl nicotinium chloride, a N-donor quaternary ammonium salt

Abstract

The new catalytic complex [MBNT][Cu4Cl5] having a synergistic effect of coordination and electrostatic interactions was found to be efficient in palladium-free copper-catalyzed Sonogashira coupling.

DABCO-functionalized silica–copper(i) complex: a novel and recyclable heterogeneous nanocatalyst for palladium-free Sonogashira cross-coupling reactions

“…[8][9][10] Recently, many studies have been conducted toward employing copper-only catalytic systems in coupling reactions, in particular, for Sonogashira-type coupling reactions. 11 A number of copper-based catalytic systems have been proposed, including bis(m-iodo)bis((À)-sparteine)dicopper(I) catalyst, 12 Cu(I)/amino acid, 13 CuI/DABCO, 14 CuCl/N-benzyl DABCO, 11 CuCl/monobenzyl nicotinium 15 and Cu(I)/diamine. 16 It should be noted that the above reaction has been performed in a homogeneous medium.…”

Visible‐Light‐Assisted Cobalt‐2‐(hydroxyimino)‐1‐phenylpropan‐1‐one Complex Catalyzed Pd/Cu‐Free Sonogashira–Hagihara Cross‐Coupling Reaction

“…So, research is currently focusing on replacing them with inexpensive and easily available metal complexes. One recent direction is concerned with employing Pd/Cu‐free catalytic systems in the Sonogashira–Hagihara cross‐coupling reaction . Cobalt‐catalyzed couplings are of interest in organic synthesis, as cobalt is low‐toxic, inexpensive, stable, and exhibits high catalytic activities.…”

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.…”