Palladium(II) complex with a potential N4-type Schiff-base ligand as highly efficient catalyst for Suzuki–Miyaura reactions in aqueous media

Banik, Biplab; Tairai, Archana; Shahnaz, Nasifa; Das, Pankaj

doi:10.1016/j.tetlet.2012.08.026

Cited by 40 publications

(13 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, an efficient Suzuki–Miyaura protocol in aqueous media is often restricted due to limited solubility and the decreased stability of the catalyst in water . Therefore, a way to improve the efficiency of Suzuki–Miyaura catalysis in water is by the employment of hydrophilic ligands …”

Section: Introductionmentioning

confidence: 99%

“…[16][17][18] Therefore, a way to improve the efficiency of Suzuki-Miyaura catalysis in water is by the employment of hydrophilic ligands. [19][20][21][22][23][24] We have recently prepared the Pd complexes cis-{L 1 PPh 2 }PdCl 2 (1) and trans-{L 2 PPh 2 } 2 PdCl 2 (2) containing different Y,C,Y pincer-type ligands L 1 (2,6-(Me 2 NCH 2 ) 2 C 6 H 3 ) À and L 2 (2,6-(tBuOCH 2 ) 2 C 6 H 3 ) À (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Amidophosphine‐stabilized palladium complexes catalyse Suzuki–Miyaura cross‐couplings in aqueous media

Jansa

Řezníček

Dostál

et al. 2016

Applied Organom Chemis

View full text Add to dashboard Cite

We report a simple and efficient procedure for Suzuki–Miyaura reactions in aqueous media catalysed by amidophosphine‐stabilized palladium complexes trans‐{L3PPh2}2PdCl2 (3), trans‐{L3PPhtBu}2PdCl2 (4), [Pd(η3‐C3H5)(L3PPh2)Cl] (5) and {Pd[2‐(Me2NCH2)C6H4](L3PPh2)Cl} (6). The acidity of the NH proton in complexes 3, 4, 5, 6 plays an important role in their catalytic activity. In addition, the palladium complexes cis‐{L1PPh2}PdCl2 (1) and trans‐{L2PPh2}2PdCl2 (2) stabilized by phosphines containing Y,C,Y‐chelating ligands L1,2 have also been found to be useful catalysts for Suzuki–Miyaura reactions in aqueous media. The method can be effectively applied to both activated and deactivated aryl bromides yielding high or moderate conversions. The catalytic activity of couplings performed in pure water increases when utilizing a Pd complex with more acidic NH protons. A decrease of palladium concentration from 1.0 to 0.5 mol% does not lead to a substantial loss of conversion. In addition, Pd complex 1 can be efficiently recovered using two‐phase system extraction. Copyright © 2016 John Wiley & Sons, Ltd.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amidophosphine‐stabilized palladium complexes catalyse Suzuki–Miyaura cross‐couplings in aqueous media

Jansa

Řezníček

Dostál

et al. 2016

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Though several reports have described the successful use of phosphine ligands with palladium complexes in catalysing Suzuki–Miyaura, Mizoroki–Heck and Sonogashira coupling reactions, these ligands have numerous limitations due to the difficulty in synthesis, high cost, toxicity and low air and moisture stability . In contrast, nitrogen‐based ligands are significantly inexpensive, easy to synthesize, non‐toxic and stable to air and moisture . Taking into consideration these substantial advantages, the interest in the use of nitrogen donor ligands with palladium to catalyse cross‐coupling reactions has been increasing rapidly.…”

Section: Introductionmentioning

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

Applied Organom Chemis

View full text Add to dashboard Cite

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.

show abstract

“…Employing conventional oil-bath heating, the coupling of more challenging aryl chlorides could be successfully accomplished at 80 ºC with the dinuclear Pd(II) complex 29 in a glycerol/water solvent mixture (Scheme 19) [68]. It is worthy of note that the use of glycerol or water alone led to the desired biphenyl products in remarkably lower yields.…”

Section: Metal-catalyzed Transformationsmentioning

confidence: 99%

Recent Advances in the Use of Glycerol as Green Solvent for Synthetic Organic Chemistry

Díaz‐Álvarez¹,

Francos²,

Croche³

et al. 2013

CGC

View full text Add to dashboard Cite

Owing to its biodegradable and non-toxic nature, glycerol, the main byproduct in the production of biodiesel fuel, is being actively investigated as a green reaction medium for synthetic organic chemistry. A huge number of synthetic transformations have been conducted in glycerol in recent years, showing most of them similar or even superior efficiency and selectivity than those performed in conventional petroleum-based organic solvents. Herein, an overview on the most recent advances reached in the field is presented. Short Running Title: Synthetic organic chemistry in glycerol

show abstract

Palladium(II) complex with a potential N4-type Schiff-base ligand as highly efficient catalyst for Suzuki–Miyaura reactions in aqueous media

Cited by 40 publications

References 54 publications

Amidophosphine‐stabilized palladium complexes catalyse Suzuki–Miyaura cross‐couplings in aqueous media

Amidophosphine‐stabilized palladium complexes catalyse Suzuki–Miyaura cross‐couplings in aqueous media

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

Recent Advances in the Use of Glycerol as Green Solvent for Synthetic Organic Chemistry

Contact Info

Product

Resources

About