Methionine: a green and efficient promoter for copper‐catalyzed Sonogashira cross‐coupling reactions

Abstract

aIn the presence of amino acids as environmentally friendly ligands, CuI-catalyzed Sonogashira cross-coupling of various aryl halides with phenylacetylene was conducted to afford the corresponding internal alkynes. L-Methionine was found to be useful for this palladium-free and amine-free coupling reaction. It was also found that the solvent system plays an important role in this reaction, and significantly affects the product formation and reaction rate. Sonogashira coupling of aryl iodides and aryl bromides in dimethylsulfoxide or dimethylformamide gave the coupled products in good to excellent yields.

Immobilized Pd on (S)‐methyl histidinate‐modified multi‐walled carbon nanotubes: a powerful and recyclable catalyst for Mizoroki–Heck and Suzuki–Miyaura C–C cross‐coupling reactions in green solvents and under mild conditions

“…All of the products are known and characterized by comparing their physical data such as FT-IR, 1 H NMR and 13 C NMR spectra with those reported in the literature. [64][65][66] The obtained results are comparable to or even higher than conversion yields compared to a reported amino palladium complex immobilized on a carbon surface. [15] To explore the leaching of the catalyst, the Heck cross-coupling reaction of bromobenzene with styrene was studied.…”

“…[49][50][51][52][53][54][55][56] In addition, MWCNTs can be used as very good catalyst supports because of their high surface area and insolubility in most solvents. [57][58][59][60][61][62][63] In continuation of our recent investigations of the application of heterogeneous catalytic systems in cross-coupling reactions, [64][65][66][67] in the work reported here, palladium was immobilized on methyl histidinate-modified MWCNTs and the catalytic activity was demonstrated by employing the Mizoroki-Heck and Suzuki-Miyaura coupling reactions. Our catalytic system results in the desired products in faster reaction times, at lower temperatures using greener solvents in comparison with conventional methods.…”

Copper-catalyzed Sonogashira reactions: advances and perspectives since 2014

“…CuI-catalyzed Sonogashira cross-coupling of different aryl halides with phenylacetylene was carried out in the presence of amino acids as ecologically friendly ligands to obtain the appropriate internal alkynes. 32 Surprisingly, this palladium-free coupling reaction worked well in the presence of L-methionine as ligand. The solvent system was also found to play a crucial role in this reaction, with a large impact on product formation and reaction rate.…”

Dicarboxylic Acid‐Functionalized MCM‐41 with Embedded Palladium Nanoparticles as an Efficient Heterogeneous Catalyst for C–C Coupling Reactions

“…[9] The Suzuki-like reaction of an acyl halide with arylboronic acid is one of the direct methods for aromatic ketone synthesis having advantages including the availability of arylboronic acids and acyl halides, high selectivity, and avoidance of using toxic carbon monoxide. [10,11] Palladium is widely applied to many coupling reactions. A number of homogeneous catalytic systems including phosphines, [12,13] palladacycle complexes, [14,15] Schiff base ligands, [16] and N-heterocyclic carbenes [17,18] have been reported for this transformation.…”

“…Consequently, variously supported palladium catalysts with improved recycling and recovery properties have been reported to overcome these shortcomings. [10,11,19,20] Because of good accessibility and porosity, mechanical stability, easy separation, relatively low cost, high thermal stability, and good catalytic performance, MCM-41 mesoporous silica material remains the most popular support choice. [21][22][23][24][25][26][27][28][29][30] In fact, the reduction of the time and energy for achieving chemical transformations and separations is the primary aim of these attempts.…”