NHC–Pd(II)–Im (NHC = N-heterocyclic carbene; Im = 1-methylimidazole) complexes as efficient catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides

Tang, Yi-Qiang; Lu, Jian‐Mei; Shao, Li‐Xiong

doi:10.1016/j.jorganchem.2011.08.042

Cited by 68 publications

(22 citation statements)

References 43 publications

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“…Furthermore, mild reactions conditions, the use of green solvents and substrate tolerance are other superior features of the Suzuki reaction. Recently, research has focused on the development of new catalyst precursors which can catalyze the coupling reactions of unactivated and cheaper aryl chlorides with low catalyst concentrations and convenient solvents . Using mixtures of water and organic solvents in the Suzuki reaction promotes solvation of mineral bases to support the Suzuki reaction by activating arylboronic acid and has the ability to dissolve organic substrates and corresponding palladium catalysts.…”

Section: Introductionmentioning

confidence: 99%

“…Shao et al . reported in a different study that Pd–NHC complexes derived from readily available starting materials such as IPr.HCl or IMes.HCl, showed high catalytic activity in the Suzuki–Miyaura coupling reactions of aryl chlorides at room temperature . However the procedures reported in the literature focused mainly on the Suzuki coupling of aryl bromides and iodides in organic solvents.…”

Section: Introductionmentioning

confidence: 99%

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Palladium(II)‐N‐heterocyclic carbene complexes: synthesis, characterization and catalytic application

Çekirdek

Yaşar

Özdemır

2014

Applied Organom Chemis

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N-Heterocyclic carbenes (NHCs) are of great importance and are powerful ligands for transition metals. A new series of sterically hindered benzimidazole-based NHC ligands (LHX) (2a-f), silver-NHC complexes (3a-f) and palladium-NHC complexes (4a-f) have been synthesized and characterized using appropriate spectroscopic techniques. Studies have focused on the development of a more efficient catalytic system for the Suzuki coupling reaction of aryl chlorides. Catalytic performance of Pd-NHC complexes and in situ prepared Pd(OAc) 2 /LHX catalysts has been investigated for the Suzuki cross-coupling reaction under mild reaction conditions in aqueous N,N-dimethylformamide (DMF). These complexes smoothly catalyzed the Suzuki-Miyaura reactions of electron-rich and electron-poor aryl chlorides.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Palladium(II)‐N‐heterocyclic carbene complexes: synthesis, characterization and catalytic application

Çekirdek

Yaşar

Özdemır

2014

Applied Organom Chemis

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“…Tang et al . reported a new type of well‐defined NHC–Pd–imidazole complexes ( C99 ) derived from IPr·HCl ( L64 ) or IMes·HCl ( L65 ), 1‐methylimidazole, and PdCl 2 showing the Suzuki coupling and amination reactions of aryl or heteroaryl chlorides in the presence of 0.01 mol% catalyst loading in high yields of up to 96% as shown in Scheme .…”

Section: N‐heterocyclic Carbenes As Ligands and Their Metal Complexesmentioning

confidence: 99%

Recent Advances in the Schiff Bases and N‐Heterocyclic Carbenes as Ligands in the Cross‐Coupling Reactions: A Comprehensive Review

Kumar

2019

Journal of Heterocyclic Chem

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Cross‐coupling reactions, namely, the Suzuki–Miyaura, Heck, Sonogashira, Hiyama, Negishi, Kumada, and Hartwig–Buchwald, are the most powerful approaches in the formation of C–C, C–N, C–O, and C–S bonds for the complex organic scaffolds in drugs, natural products, organic materials, and fine chemicals. The nitrogen‐based ligands have upper hands in these reactions because they are air stable, inexpensive, and easier to handle than the phosphorous counterparts. In this perspective, Schiff bases and N‐heterocyclic carbenes have been explored extensively in terms of novel design and preparation as ligands in the coupling reactions. Facile recovery and reusability of these ligands make them eco‐friendly and economical. A comprehensive outline on the progress in Schiff bases–metal complexes and NHC–metal complexes that mediated cross‐coupling reactions with recent examples highlighted is reported (160 references).

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“…Their palladium complexes are equal, and in some cases even superior, to the corresponding phosphine‐containing catalysts and they are known as one of the best choices as catalyst for coupling reactions . During the past decades, NHC and their metal complexes, usually with higher air‐ and thermal‐stability, have attracted much attention in the palladium‐catalyzed Heck, Suzuki‐Miyaura and Hiyama cross‐coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Magnetic Mesoporous SBA‐15 Functionalized with a NHC Pd(II) Complex: An Efficient and Recoverable Nanocatalyst for Hiyama Reaction

et al. 2019

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Magnetite nanoparticles (MNPs) were covered by a silica shell and then embedded into mesoporous silica . Magnetic mesoporous silica (Fe 3 O 4 @SiO 2 -SBA) was then reacted with 3chloropropyltriethoxysilane (CPTS), sodium salt of imidazole and 2-bromopyridine to give Fe 3 O 4 @SiO 2 -SBA functionalized with 3-(pyridin-2-yl)-1H-imidazol-3-ium-propyl (PIP) as a supported pincer ligand for Pd(II). The functionalized magnetic mesoporous silica were then treated with t-BuOK at À 80°C in THF and then reacted with [PdCl 2 (SMe 2 ) 2 ] to give supported Pd (II)-carbene complex containing C,N-bidentate ligand. The chloride ions were then exchanged by bromide ions using a NaBr solution of diethylether/acetone mixture. The prepared catalyst was characterized with, FT-IR, thermo gravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), Brunauer-Emmett-Teller surface area measurement (S BET ), energy dispersive X-ray analysis (EDX) and wide angle X-ray diffraction spectroscopy (XRD). The prepared magnetic catalyst was effectively used in the coupling reaction of triethoxyphenylsilane with aryl halides (Hiyama reaction) in the presence of a base. The reaction parameters such as solvents, amount of catalyst, base and temperature were optimized. The catalyst was then magnetically decanted, washed, and reused several times.

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NHC–Pd(II)–Im (NHC = N-heterocyclic carbene; Im = 1-methylimidazole) complexes as efficient catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides

Cited by 68 publications

References 43 publications

Palladium(II)‐N‐heterocyclic carbene complexes: synthesis, characterization and catalytic application

Palladium(II)‐N‐heterocyclic carbene complexes: synthesis, characterization and catalytic application

Recent Advances in the Schiff Bases and N‐Heterocyclic Carbenes as Ligands in the Cross‐Coupling Reactions: A Comprehensive Review

Magnetic Mesoporous SBA‐15 Functionalized with a NHC Pd(II) Complex: An Efficient and Recoverable Nanocatalyst for Hiyama Reaction

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