Synthesis of heterobiaryls via Suzuki‐Miyaura coupling reaction of potassium aryltrifluoroborates with heteroaryl halides in aqueous systems

Abstract

A variety of heterobiaryl compounds have been synthesized by the Suzuki‐Miyaura coupling reactions of heteroaryl halides with potassium aryltrifluoroborates. Pd (OAc)2 was found to be highly efficient for the Suzuki‐Miyaura coupling reactions of various heteroaryl halides with potassium aryltrifluoroborates in aqueous systems, delivering the corresponding heterobiaryl compounds in good to excellent yields.

Suzuki–Miyaura arylation of 2,3‐, 2,4‐, 2,5‐, and 3,4‐dibromothiophenes

“…The superior catalytic activity of Pd(OAc) 2 has been also shown in Suzuki–Miyaura reaction of aryltrifluoroborate derivatives in aqueous media. [ 33 ] Based on these results, for further studies, we chose Pd(OAc) 2 as a catalyst and 95% EtOH as a green and inexpensive solvent.…”

“…Typically, the reaction is carried out in toluenewater with an inorganic base. [4,9,16,34] Although other solvents can be used as well (DMF, [35,36] dioxane, [37,38] or EtOH [33] ), it has been demonstrated that scope of boronic acids and thiophene substitution patterns is much more narrow. One notable exception is a method proposed by Varello et al [35] with catalysis by Pd(PPh 3 ) 4 in the presence of Na 2 CO 3 in DMF-water.…”

“…It was demonstrated to work both with 2,3-and 2,4-dibromothiophenes, but at the same time, yields of 2,3-diaryl derivatives were twice lower, compared with 2,4-diarylthiophene analogues with the same boronic acids. Among palladium catalysts, mainly Pd(OAc) 2 (with [9,16] or without [33,36] ligand) and Pd(PPh 3 ) 4 were used. [4,35,37,38] Very high efficiency was achieved in the reaction catalyzed by Pd(OAc) 2 (0.04 mol %) without any ligand, but it required 4 equiv.…”

“…As cross‐coupling of an aryl potassium trifluoroborate with a dihalothiophene provided only a moderate yield, [ 33 ] we have focused on more affordable boronic acids. Typically, the reaction is carried out in toluene–water with an inorganic base.…”

Immobilization of Au nanoparticles on poly(glycidyl methacrylate)‐functionalized magnetic nanoparticles for enhanced catalytic application in the reduction of nitroarenes and Suzuki reaction

“…[20][21][22] The Suzuki-Miyaura reaction is usually performed by palladium catalyst. [23][24][25][26] Ni and Cu catalysts have also been used for this reaction but they have low yields. [27,28] Au catalysts have also exhibited high catalytic activity in the Suzuki reaction.…”