Pd nanoparticles on reverse phase silica gel as recyclable catalyst for Suzuki-Miyaura cross coupling reaction and hydrogenation in water

Shabbir, Saira; Lee, Sinyoung; Lim, Myung-Seop; Lee, Heejin; Ko, Hyeji; Lee, Youngbok; Rhee, Hakjune

doi:10.1016/j.jorganchem.2017.07.003

Cited by 44 publications

(18 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interestingly, this high yields were also maintained when phenylboronic acid was replaced with p -tolyl- or p -chloroboronic acid (Entry 7 & 8). Moreover, at an elevated temperature (80°C) and with an extended reaction time our system can also tolerates difficult substrates like sterically demanding 2-iodotoluene (entry 10) and 1-bromo-2,5-dimethoxybenzene (entry 11), or heteroaryl halides like 3-iodopyridine (entry 12) or 5-bromopyrimidine (entry 13) and provided the cross-coupling products in good-to-excellent yields.It needs to mention that aturnover number (TON) close to 1000 was obtainedwith our catalyst for cross-coupling with a few aryl bromides in water,and this value is either comparable[ 44 ] or superior [ 45 ]with some of the reported PdNPs-based catalysts that are chemically synthesized. Unfortunately, despite good results with aryl bromides or aryl iodides, our catalyst is not suitable for activating aryl chlorides as substrate (Entry 15 & 16).Noteworthy to mention that usually aryl chlorides are difficult substrates to be activated in Suzuki reaction because of stronger C-Cl bond compared to C-Br or C-I bond [ 9 ].…”

Section: Resultsmentioning

confidence: 61%

Biogenic synthesis of palladium nanoparticles and their applications as catalyst and antimicrobial agent

et al. 2017

View full text Add to dashboard Cite

This paper describes a simple in-situ process of synthesizing highly dispersed palladium nanoparticles (PdNPs) using aqueous leaf extract of GarciniapedunculataRoxb as bio-reductant and starch (0.3%) as bio-stabilizer. The PdNPs are characterized by techniques like FTIR, TEM, SEM-EDX, XRD and XPS analysis. It is worthnoting thatwhen the synthesis of nanoparticles was carried out in absence of starch, agglomeration of particles has been noticed.The starch-assisted PdNPs showed excellent aqueous-phase catalytic activities for three important reactions: the Suzuki-Miyaura cross-coupling reactions of aryl halides (aryl bromides and iodides) with arylboronic acids; selective oxidations of alcohols to corresponding carbonyl compounds; and reduction of toxic Cr(VI) to nontoxic Cr(III). Our catalyst could be reused up to four cycles without much compromising with its activity. Furthermore, the material also demonstrated excellent antimicrobial and anti-biofilm activities against a novel multidrug resistant clinical bacterial isolate Cronobactersakazakii strain AMD04. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of PdNPswere found to be 0.06 and 0.12 mM respectively.

show abstract

Section: Resultsmentioning

confidence: 61%

Biogenic synthesis of palladium nanoparticles and their applications as catalyst and antimicrobial agent

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Other metals were chosen to prepare complexes, namely Cu(I) with R 1 = H and several R 2 chains, which were active in MMA polymerization [7]. Palladium nanoparticles with IMP supported in functionalized silica were characterized and shown to be active in Suzuki-Miyaura cross coupling reactions and hydrogenation in water [8]. Another recent report addressed the selective oxidative cleavage of 1-octene catalyzed by arene Ru(II) complexes of R 1 ,R 2 -IMP (R 1 = H, R 2 = functionalized chains) [9].…”

Section: Introductionmentioning

confidence: 99%

New Molybdenum(II) Complexes with α-Diimine Ligands: Synthesis, Structure, and Catalytic Activity in Olefin Epoxidation

et al. 2019

View full text Add to dashboard Cite

Three new complexes [Mo(η3-C3H5)Br(CO)2{iPrN=C(R)C5H4N}], where R = H (IMP = N-isopropyl 2-iminomethylpyridine), Me, and Ph, were synthesized and characterized, and were fluxional in solution. The most interesting feature was the presence, in the crystal structure of the IMP derivative, of the two main isomers (allyl and carbonyls exo), namely the equatorial isomer with the Br trans to the allyl and the equatorial with the Br trans to one carbonyl, the position trans to the allyl being occupied by the imine nitrogen atom. For the R = Me complex, the less common axial isomer was observed in the crystal. These complexes were immobilized in MCM-41 (MCM), following functionalization of the diimine ligands with Si(OEt)3, in order to study the catalytic activity in olefin epoxidation of similar complexes as homogeneous and heterogeneous catalysts. FTIR, 13C- and 29Si-NMR, elemental analysis, and adsorption isotherms showed that the complexes were covalently bound to the MCM walls. The epoxidation activity was very good in both catalysts for the cis-cyclooctene and cis-hex-3-en-1-ol, but modest for the other substrates tested, and no relevant differences were found between the complexes and the Mo-containing materials as catalysts.

show abstract

“…The synthetic strategy is green and environmentally benign as it avoids the use of external reducing agents, which is common among many reports. 19−21 The ternary hybrid was successfully demonstrated in water for causing industrially important Suzuki C–C coupling, for reducing the nitroaromatic compounds to give industrially useful amino-based precursors, and for the degradation of the organic dyes.…”

Section: Introductionmentioning

confidence: 99%

Calixarene-Assisted Pd Nanoparticles in Organic Transformations: Synthesis, Characterization, and Catalytic Applications in Water for C–C Coupling and for the Reduction of Nitroaromatics and Organic Dyes

2019

View full text Add to dashboard Cite

A new type of ternary hybrid, Pd@MCM-Calix ox , based on mesoporous silica, calixarene conjugate, and Pd(0) nanoparticles (NPs) was synthesized by sacrificial oxidation of allylic calixarene conjugate eventually functionalized with mesoporous silica without using any external reducing agent. The role of the calix conjugate in the formation of Pd@MCM-Calix ox has been established. The hybrid, Pd@MCM-Calix ox , was characterized by different techniques to support the formation of well-dispersed Pd(0) NPs of 12 ± 2 nm size. The catalyst, Pd@MCM-Calix ox , has been proven to be a resourceful one in water in three different types of reactions, namely, Suzuki C–C cross coupling, reduction of both hydrophilic and hydrophobic nitroaromatic compounds, and reduction and degradation of cationic, anionic, and neutral organic dyes. The catalyst exhibited higher turnover frequencies for all these transformations even when a very low concentration of Pd-based catalyst was used. The Pd@MCM-Calix ox hybrid catalyst can be recycled several times without experiencing any significant loss in the activity. Also, the regenerated catalyst showed retention of well-spread Pd(0) species even after several catalytic cycles. The tetraallyl calixarene, allylCalix, conjugate acts as a reducing agent, also controls the size, and yields the well-dispersed Pd(0) NPs. The calix conjugate further provides a hydrophobic core in assisting the diffusion of hydrophobic substrates toward catalytic sites.

show abstract

Pd nanoparticles on reverse phase silica gel as recyclable catalyst for Suzuki-Miyaura cross coupling reaction and hydrogenation in water

Cited by 44 publications

References 52 publications

Biogenic synthesis of palladium nanoparticles and their applications as catalyst and antimicrobial agent

Biogenic synthesis of palladium nanoparticles and their applications as catalyst and antimicrobial agent

New Molybdenum(II) Complexes with α-Diimine Ligands: Synthesis, Structure, and Catalytic Activity in Olefin Epoxidation

Calixarene-Assisted Pd Nanoparticles in Organic Transformations: Synthesis, Characterization, and Catalytic Applications in Water for C–C Coupling and for the Reduction of Nitroaromatics and Organic Dyes

Contact Info

Product

Resources

About