Suzuki–Miyaura Coupling of Aryl Sulfonates with Arylboronic Acids Using a Morpholine–Pd(OAc)₂ Catalyst System

Abstract

We report a new catalyst system, a morpholine–Pd(OAc)2 complex, for Suzuki–Miyaura coupling of aryl tosylates or mesylates with arylboronic acids to give biaryl compounds. The morpholine–Pd(OAc)2 catalyst system is proposed to be a precursor of the catalytically active species in the coupling reaction. Aryl chlorides and aryl triflates can also be used in this coupling reaction. Altogether, 22 biaryl compounds were obtained using this catalyst system.

Novel glycosyl pyridyl-triazole@palladium nanoparticles: efficient and recoverable catalysts for C–C cross-coupling reactions

“…The Suzuki-Miyaura reaction is among the most important coupling reactions for synthetic organic and process chemistry including pharmaceuticals, agricultural chemicals and sophisticated materials. [25][26][27][28][29][30] The coupling reaction of 4-iodoanisole with phenylboronic acid was used as a model reaction to optimize the reaction conditions, including the catalyst, base, and solvent. As shown in Table 1, different amounts of catalyst 5a between 0.01-0.1 mol% were investigated first for this reaction, and 0.025 mol% loading of Pd was found to be optimal.…”

Suzuki–Miyaura Coupling of Aryl Chlorides with Arylboronic Acids Using the Morpholine–NiCl2 Catalyst System

“…1‐Methoxy‐4‐(4′‐ tert ‐butylphenyl)benzene (3h): 23 Following the general procedure, using 4‐chloroanisole (0.50 mmol) and (4‐ tert ‐butylphenyl)boronic acid (0.60 mmol), after 14 h at 80 °C, flash chromatography ( n ‐hexane/ethyl acetate, 25:1→10:1) gave 38.0 mg (0.158 mmol, 32 %) of the title compound as a white solid, m.p. 136–137 °C.…”

“…1‐(4′‐Methoxybiphenyl‐2‐yl)ethanone (3n): 23 Following the general procedure, using 2′‐chloroacetophenone (0.50 mmol) and (4‐methoxyphenyl)boronic acid (0.60 mmol), after 14 h at 80 °C, flash chromatography ( n ‐hexane/ethyl acetate, 15:1) gave 41.0 mg (0.181 mmol, 36 %) of the title compound as a pale‐yellow oil. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.53 (d, J = 7.8 Hz, 1 H), 7.49 (d, J = 7.8 Hz, 1 H), 7.39 (dd, J = 6.8, 6.8 Hz, 2 H), 7.28 (d, J = 8.5 Hz, 2 H), 6.97 (d, J = 7.7 Hz, 2 H), 3.86 (s, 3 H), 2.03 (s, 3 H) ppm.…”

“…We recently described the use of the morpholine–Pd(OAc) 2 system for the Suzuki–Miyaura coupling of aryl sulfonates with arylboronic acids,23 and this system is also applicable to aryl chlorides. In this work we have applied this system to nickel and found that the new morpholine–NiCl 2 system is effective for the Suzuki–Miyaura coupling of aryl chlorides.…”

Electrochemical Synthesis of Pd Nano Particles on Pencil-Graphite and Application for Suzuki Coupling Reactions

“…Various palladium based homogeneous catalysts such as palladium diaminocarbene complexes [6], oxime based palladacycle [7], chalcogenated Schiff base [8], some nitrogen based ligands [9], N-H heterocyclic carbene complex [10] and morpholine-Pd(OAc) 2 [11] were employed in the Suzuki cross coupling reactions. However, these reported catalysts could not be recovered and hence, researchers moved towards heterogeneous supports like alumina based catalyst [12], MCM-41 [13], MIL-101 [14], Al-MOF [15], Montmorillonite clay [16], sepiolite clay [17], SBA-15/ CCMet/Pd(II) [18], Pd acetate in imine functionalized silica gel [19], and nanoporus polymeric ionic liquid loaded with palladium [20].…”