Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex

An efficient catalytic system using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride and palladium chloride ((BeDABCO) 2 Pd 2 Cl 6 ) was developed for the Sonogashira reaction. In the presence of a catalytic amount of this efficient, stable homogeneous catalytic system that is non-sensitive to air and moisture, various aryl halides were efficiently coupled with phenylacetylene in good yields in H 2 O at 50°C under copper-free conditions. Benzyl dabco as an efficient ligand and also a quaternary ammonium salt had an efficient stabilizing effect on the Pd(0) species.

Section: Methodssupporting

confidence: 62%

(BeDABCO)₂Pd₂Cl₆ as an efficient homogeneous catalyst for copper‐free Sonogashira cross‐coupling reaction

Hajipour

Rafiee

2014

“…The spectrum of the MNPs alone shows a stretching vibration at 3381 cm −1 which incorporates the contributions from both symmetric and asymmetric modes of the OH bonds which are attached to the surface of iron atoms . The bands at low wavenumbers (≤700 cm −1 ) arise from vibrations of FeO bonds of iron oxide, which for the bulk Fe 3 O 4 samples appear at 570 and 375 cm −1 but for Fe 3 O 4 NPs at 624 and 572 cm −1 , a blue shift due to the size reduction . The presence of an adsorbed water layer is confirmed by a stretching vibrational mode of water at 1622 cm −1 .…”

Section: Resultsmentioning

confidence: 86%

Palladium immobilized on amidoxime‐functionalized magnetic Fe₃O₄ nanoparticles: a highly stable and efficient magnetically recoverable nanocatalyst for sonogashira coupling reaction

Veisi

Sedrpoushan

Maleki

et al. 2015

We describe the synthesis of a novel Fe 3 O 4 /amidoxime (AO)/Pd nanocatalyst by grafting of AO groups on Fe 3 O 4 nanoparticles and subsequent deposition of Pd nanoparticles. Prior to grafting of AO, the 2-cyanoethyl-functionalized Fe 3 O 4 nanoparticles prepared through combining 2-cyanoethyltriethoxysilane and Fe 3 O 4 were treated with hydroxylamine. The AO-grafted Fe 3 O 4 nanoparticles were then used as a platform for the deposition of Pd nanoparticles. The catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, scanning and transmission electron microscopies, vibrating sample magnetometry, wavelength-and energy-dispersive X-ray spectroscopies and inductively coupled plasma analysis. Fe 3 O 4 /AO/Pd is novel phosphine-free recyclable heterogeneous catalyst for Sonogashira reactions. Interestingly, the novel catalyst could be recovered in a facile manner from the reaction mixture by applying an external magnet device and recycled seven times without any significant loss in activity.Fe 3 O 4 /AO/Pd as an effective nano catalyst in the sonogashira reaction

“…We examined the Mizoroki–Heck coupling reaction by considering Pd‐BOX complexes ( Pd-BOX-2 and Pd-BOX-3 ) and commercially available palladium complexes having bidentate nitrogen donor ligands (PdCl 2 ‐Bipy and PdCl 2 ‐Phen; Fig. ) and also Pd(PPh 3 ) 2 Cl 2 and Pd(PhCN) 2 Cl 2 under the optimized experimental conditions . All Pd‐BOX complexes give again excellent isolated yields (97–98%) of product (Table , entries 8 and 9).…”

Section: Resultsmentioning

confidence: 99%

A highly active palladium(II)–bis(oxazoline) catalyst for Suzuki–Miyaura, Mizoroki–Heck and sonogashira coupling reactions in aqueous dimethylformamide

Ibrahim

Ali

Fettouhi

et al. 2015

An efficient catalytic system based on a new palladium-bis(oxazoline) (Pd-BOX-1) complex has been developed. The complex Pd-BOX-1 adopts a legless chair-type structure where the distorted square planar [PdN 2 Cl 2 ] moiety and the benzene ring spacer represent the seat and the chair back, respectively. The catalytic activity of Pd-BOX-1 has been investigated in dimethylformamide-water under aerobic and mild conditions in Suzuki-Miyaura coupling reactions of arylboronic acids with aryl iodides, aryl bromides and aryl chlorides, Mizoroki-Heck coupling reactions of aryl halides with styrene derivatives, and Sonogashira coupling reactions of aryl halides with terminal alkynes. A wide range of functional groups as substituents on the arylboronic acids and aryl halides were considered. Pd-BOX-1 demonstrates exceptional air and moisture stability. Of note, the catalyst system based on Pd-BOX-1 shows high recycling ability in Suzuki-Miyaura coupling reactions in dimethylformamide-water without any loss in catalytic activity.