Importance of some factors on the Suzuki‐Miyaura cross‐coupling reaction

Abstract

This review was designed to give an overview of the significant parameters in Suzuki‐Miyaura coupling (SMC) reactions, which are a powerful tool for the formation of the carbon–carbon (CC) bond. Since the SMC reaction depends on factors such as solvent, base, temperature, time, catalyst amount, substituent in aryl halides, and molar ratios of the substrates, all these parameters should be screened for a successful SMC reaction. After finding the optimum reaction conditions, the SMC reaction's products of boronic acid derivatives with aryl halides can be obtained in high yields.

GrafeoPlad Palladium: Insight on Structure and Activity of a New Catalyst Series of Broad Scope

“…Due to the the stronger carbon halide bond determined by the higher halogen electronegativity (in the order Cl, 3.16 > Br, 2.96 > I, 2.66), the latter lower reactivity of bromobenzene is well‐known and general for cross‐coupling reactions. [ 17 ] Similarly, the fact that methanol is a far better reaction medium when compared to acetonitrile is due to the well‐known need for protic solvents in the Suzuki–Miyaura reaction. [ 17 ] The kinetic profile of the Suzuki–Miyaura reaction in MeOH for iodobenzene cross‐coupling shows ( Figure , left) the typical sigmoidal shape, with a first rapid reaction rate within the first 40 min of reaction, followed by a substantially slower reaction in the second time period (1–3 h).…”

“…[ 17 ] Similarly, the fact that methanol is a far better reaction medium when compared to acetonitrile is due to the well‐known need for protic solvents in the Suzuki–Miyaura reaction. [ 17 ] The kinetic profile of the Suzuki–Miyaura reaction in MeOH for iodobenzene cross‐coupling shows ( Figure , left) the typical sigmoidal shape, with a first rapid reaction rate within the first 40 min of reaction, followed by a substantially slower reaction in the second time period (1–3 h). While the reaction with iodobenzene proceeds nearly to completion, in the case of bromobenzene the yield reaches a maximum 56.4% value after which no further conversion of the substrate is observed.…”

Molecular Organosulphur, Organoselenium and Organotellurium Complexes as Homogeneous Transition Metal Catalytic Systems for Suzuki Coupling

“…During the last few years, several reviews and perspective articles have been published focusing different aspects of its catalysis. Such developments include ligand‐free catalysis, [108] selection of boron reagents, [109] Suzuki Miyaura coupling in green medium, [8] effect of various factors such as time, temperature, solvent and base on Suzuki [111] development of new classes of catalytic systems [9–17] and reduction in the catalyst loading [14] . However, after year 2013, no consolidated review or perspective article has been published on the progress in designing the catalytic systems using organochalcogen ligands for this reaction.…”

Organosulphur, organoselenium and organotellurium compounds for the development of heterogeneous and nanocatalytic systems for Suzuki coupling

“…18,19,25,30,58,62 During the last few years, several review and perspective articles have been published focussing on different aspects of Suzuki catalysis. Developments include ligand-free catalysis, 108 selection of boron reagents, 109 usage of magnetically retrievable catalysts, 110 Suzuki-Miyaura coupling in green medium, 7 effect of various factors such as time, temperature, solvent and base on Suzuki 111 development of new classes of catalytic systems, 2,[10][11][12][13][14][15][16][17] and reduction in the catalyst loading. 14 In 2013, the first perspective article was published about the development of catalytic systems using organosulphur and related ligands.…”