A green method for the synthesis of gelatin/pectin stabilized palladium nano-particles as efficient heterogeneous catalyst for solvent-free Mizoroki–Heck reaction

Khazaei, Ardeshir; Khazaei, Marzieh; Rahmati, Sadegh

doi:10.1016/j.molcata.2014.12.013

Cited by 48 publications

(20 citation statements)

References 52 publications

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“…Among several aspects of green chemistry, removal of volatile organic solvents from the reaction medium (i.e., use of solvent-free conditions) is of utmost importance. Furthermore, in many cases, solvent-free technique offers considerable synthetic advantages in terms of yield, selectivity, and simplicity of reaction procedure [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

et al. 2016

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The aim of this work is to introduce a novel and attractive protic acidic ionic liquid as catalyst for organic synthesis. To achieve this aim, N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et 3 N-SO 3 H]HSO 4 } was prepared by reaction of NEt 3 with ClSO 3 H and then with H 2 SO 4 . The novel acidic ionic liquid was identified by Fourier-transform infrared (FT-IR), 1 H nuclear magnetic resonance (NMR), 13 C NMR, and mass spectroscopies. Its catalytic activity was then examined in the cross-aldol condensation reaction of arylaldehydes with cycloalkanones under solvent-free conditions, obtaining a,a 0 -bis(arylidene)cycloalkanones in high yield after short reaction time. Graphical AbstractKeywords Protic acidic ionic liquid Á N,N-Diethyl-N-sulfoethanaminium hydrogen sulfate {[Et 3 N-SO 3 H]HSO 4 } Á a,a 0 -Bis(arylidene)cycloalkanone Á Crossaldol condensation Á Solvent-free & Abdolkarim Zare

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Section: Introductionmentioning

confidence: 99%

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

et al. 2016

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“…To the best of our knowledge, this is the first example of neat Mizoroki-Heck reaction for the formation of dienes. The vinylation of acrylic substrates has been already reported in solvent-free conditions but it usually requires the use of a ligand, palladium supported catalyst, palladium nanocatalyst or microwave activation [50][51][52][53][54][55][56][57]. Finally, 2 was introduced in excess, in one portion or in sequential addition, without improving the yield (entries 10 and 11).…”

Section: Optimization Of the Mizoroki-heck Reactionmentioning

confidence: 99%

Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

2018

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Abscisic acid (ABA) is a natural product, which is a well-known phytohormone. However, this molecule has recently exhibited interesting biological activities, emphasizing the need for a simple and direct access to new analogues based on the ABA framework. Our strategy relies on a pallado-catalyzed Mizoroki-Heck cross-coupling as key reaction performed in solvent and ligand free conditions. After a careful optimization, we succeeded in accessing various (E/Z)-dienes and (E/E/Z)-trienes in moderate to good yields without isomerization and applied the same approach to the synthesis of ABA in an environmentally sound manner.

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“…The use of bare‐metal oxides as supports for Pd‐NPs has become limited because, the metal oxides may be sensitive to the oxidation of organic substrates and sometimes themselves may act as catalysts result in unwanted products. [ 3a,8 ] The carbohydrate‐based biopolymers such as agarose, [ 9 ] alginate, [ 10 ] arabinogalactan, [ 11 ] cellulose, [ 12 ] chitosan, [ 13 ] lignin, [ 14 ] pectin [ 15 ] and starch [ 16 ] were used for stabilization of M‐NPs. These biopolymers found highly favorable stabilizers for M‐NPs because they are naturally‐abundant, sustainable, non‐toxic, biodegradable and hence eco‐friendly.…”

Section: Introductionmentioning

confidence: 99%

Fe₃O₄‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions

Bharamanagowda

Kumar

2020

Applied Organom Chemis

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Palladium nanoparticles (Pd‐NPs) were synthesized under green conditions in water by chemical reduction of PdCl2 with NaOH and supported by Fe3O4‐Lignin. Fe3O4‐Lignin is an organic–inorganic hybrid core‐shell was synthesized by sonication of a mixture of Fe3O4‐NPs (20 nm) and alkali lignin. The new materials Fe3O4‐Lignin and Fe3O4‐Lignin@Pd‐NPs were characterized by PXRD, SEM and FT‐IR spectroscopy. The Fe3O4‐Lignin@Pd‐NPs was further confirmed by UV–Visible spectroscopy, TEM, EDX, HRICP‐AES and TGA/DTA. The average size of Pd‐NPs determined from PXRD was 5–10 nm. The amount of palladium loaded on Fe3O4‐Lignin obtained from EDX analysis was 26.63% by mass. The amount of Fe and Pd present in the catalyst obtained from HRICP‐AES was 11.88 (wt. %) and 10.90 (wt. %) respectively per gram of lignin. The catalytic potential of Fe3O4‐Lignin@Pd‐NPs was evaluated in Mizoroki‐Heck C‐C coupling reaction. During the optimization studies of reaction between iodobenzene and n‐butyl acrylate in various solvents and under solvent‐free but aerobic conditions using various inorganic and organic bases, the product n‐butyl 3‐phenylprop‐2‐enoate (1a) obtained was as high as 95% in highly polar solvents as short as in 10 min and 99% under solvent‐free conditions in 3 min at 140 °C using n‐Pr3N as base. The scope of the above catalyst was investigated in the Mizoroki‐Heck reaction of various aryl/heterocyclic halides and n‐butyl acrylate/styrene under optimized solvent‐less conditions. The corresponding products were obtained in high yields (73–99%). The catalyst recovered by magnetic decantation was reused for five times in the C‐C coupling reaction between iodobenzene and n‐butyl acrylate which yielded 90–95% of the desired product, 1a.

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A green method for the synthesis of gelatin/pectin stabilized palladium nano-particles as efficient heterogeneous catalyst for solvent-free Mizoroki–Heck reaction

Cited by 48 publications

References 52 publications

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

Fe₃O₄‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions

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A green method for the synthesis of gelatin/pectin stabilized palladium nano-particles as efficient heterogeneous catalyst for solvent-free Mizoroki–Heck reaction

Cited by 48 publications

References 52 publications

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

Solvent-Free Mizoroki-Heck Reaction Applied to the Synthesis of Abscisic Acid and Some Derivatives

Fe3O4‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions

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Fe₃O₄‐Lignin@Pd‐NPs: A highly efficient, magnetically recoverable and recyclable catalyst for Mizoroki‐Heck reaction under solvent‐free conditions