Silica Chloride Mediated Alkylation of Electron-rich Aromatics by Benzyl or tert-Butyl Chloride

Mohanazadeh, Farajollah; Amini, Homira

doi:10.5012/bkcs.2010.31.10.3038

Cited by 6 publications

(4 citation statements)

References 22 publications

(10 reference statements)

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“…Several solvents with appropriate boiling points were tested and PhCF 3 turned out to be the best choice (Table 1, entries 2-4). Later, the optimization of the reaction conditions focused on the screening of ligands (Table 1, entries [5][6][7][8][9][10][11][12] and Pd catalysts (Table 1, entries [13][14][15][16]. As a result, Pd(PPh 3 ) 4 and Xantphos were found to be the best combination for this transformation.…”

Section: Resultsmentioning

confidence: 99%

“…While most direct alkylation reactions of furans fall into two types: (1) Friedel-Cras alkylation, which usually requires Lewis acids/environmentally harmful solvents [5][6][7] and has low selectivity and yields for furans; (2) nucleophilic substitution reactions, which need extremely low temperature conditions and strong base to form and stabilize the furan anion. [8][9][10] Both types of reactions suffer from the limitation of functional group compatibility.…”

Section: Introductionmentioning

confidence: 99%

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Regioselective Pd-catalyzed α-alkylation of furans using alkyl iodides

2021

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Regioselective Pd-catalyzed α-alkylation of furans using alkyl iodides

2021

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“…Interparticle porosity resulted in relatively large pore volume (1.2 cm 3 /g). Preliminarily, silica was converted to silica chloride (Si-Cl) in the presence of thionyl chloride, as has already been described in the literature [56,57], and the resulting chloride ions were titrated with a silver nitrate solution in the presence of a potassium chromate solution, used as an indicator. 6 I amino-6 I -deoxy-β-CD was then reacted to obtain the Si-NH-CD derivatives.…”

Section: Resultsmentioning

confidence: 99%

Sonochemically-Promoted Preparation of Silica-Anchored Cyclodextrin Derivatives for Efficient Copper Catalysis

et al. 2019

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Silica-supported metallic species have emerged as valuable green-chemistry catalysts because their high efficiency enables a wide range of applications, even at industrial scales. As a consequence, the preparation of these systems needs to be finely controlled in order to achieve the desired activity. The present work presents a detailed investigation of an ultrasound-promoted synthetic protocol for the grafting of β-cyclodextrin (β-CD) onto silica. Truly, ultrasound irradiation has emerged as a fast technique for promoting efficient derivatization of a silica surface with organic moieties at low temperature. Three different β-CD silica-grafted derivatives have been obtained, and the ability of β-CD to direct and bind Cu when CD is bonded to silica has been studied. A detailed characterization has been performed using TGA, phenolphthalein titration, FT-IR, diffuse reflectance (DR), DR UV-Vis, as well as the inductively-coupled plasma (ICP) of the β-CD silica-grafted systems and the relative Cu-supported catalysts. Spectroscopic characterization monitored the different steps of the reaction, highlighting qualitative differences in the properties of amino-derivatized precursors and final products. In order to ensure that the Cu-β-CD silica catalyst is efficient and robust, its applicability in Cu(II)-catalyzed alkyne azide reactions in the absence of a reducing agent has been explored. The presence of β-CD and an amino spacer has been shown to be crucial for the reactivity of Cu(II), when supported.

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“…We determined the amount of chloropropylsilyl groups on the surface of GO using Mohr's method (see ESI †). 56,57 The total density of chloropropylsilyl groups on GO was estimated to be about 0.95 mmol g À1 . The chloropropylsilyl groups not only cover the GO sheets but also make them ready for further surface functionalization.…”

Section: Methodsmentioning

confidence: 99%

Palladium decorated on a new dendritic complex with nitrogen ligation grafted to graphene oxide: fabrication, characterization, and catalytic application

Golestanzadeh

Naeimi

2019

RSC Adv.

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Immobilized Pd nanoparticles on a new ligand, namely, tris(pentaethylene-pentamine)triazine supported on graphene oxide (Pd np -TPEPTA (L) -GO) was introduced as a novel and robust heterogeneous catalyst for use in C-C bond formation reaction. The Pd np -TPEPTA (L) -GO catalyst was synthesized by complexation of Pd with TPEPTA as a ligand with high N-ligation sites that were supported on graphene oxide through 3chloropropyltrimethoxysilane. The prepared catalyst was characterized using some microscopic and spectroscopic techniques. The TPEPTA (L) -GO substrate is a 2D heterogeneous catalyst with a high specific surface area and a large amount of N-ligation sites. The Pd np -TPEPTA (L) -GO catalyst used in the C-C bond formation reaction between aryl or heteroaryl and phenylboronic acid derivatives was applied towards the synthesis of biaryl units in high isolated yields. Notably, a series of competing experiments were performed to establish the selectivity trends of the presented method. Also, this catalyst system was reusable at least six times without a significant decrease in its catalytic activity.

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Silica Chloride Mediated Alkylation of Electron-rich Aromatics by Benzyl or tert-Butyl Chloride

Cited by 6 publications

References 22 publications

Regioselective Pd-catalyzed α-alkylation of furans using alkyl iodides

Regioselective Pd-catalyzed α-alkylation of furans using alkyl iodides

Sonochemically-Promoted Preparation of Silica-Anchored Cyclodextrin Derivatives for Efficient Copper Catalysis

Palladium decorated on a new dendritic complex with nitrogen ligation grafted to graphene oxide: fabrication, characterization, and catalytic application

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