Use of Monosaccharides in Metal-Catalyzed Coupling Reactions

Kyne, Sara H.; Camp, J. E.

doi:10.1021/acssuschemeng.6b01914

Cited by 10 publications

(5 citation statements)

References 90 publications

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“…Naturally occurring substrates (NOSs) such as starch, cyclodextrins, cellulose, chitosan, agarose, pectin, etc. are good candidates to be used as supports to provide an environmentally benign and practical palladium–catalyst system. − In addition to a support role for NOSs, they can act as a reducing agent to form metal nanoparticles and stabilize them . These materials have received considerable attention due to having potential in the design of heterogeneous Pd–catalyst systems with high reactivity and selectivity in environmentally benign/acceptable media.…”

Section: Introductionmentioning

confidence: 99%

“…20−32 In addition to a support role for NOSs, they can act as a reducing agent to form metal nanoparticles and stabilize them. 31 These materials have received considerable attention due to having potential in the design of heterogeneous Pd−catalyst systems with high reactivity and selectivity in environmentally benign/acceptable media. Other interesting features of NOSs are abundant availability, low price, environmental friendliness, and structure diversity.…”

Section: ■ Introductionmentioning

confidence: 99%

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Supported Palladium on Magnetic Nanoparticles–Starch Substrate (Pd-MNPSS): Highly Efficient Magnetic Reusable Catalyst for C–C Coupling Reactions in Water

Tukhani

Panahi

Khalafi-Nezhad

2017

ACS Sustainable Chem. Eng.

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A novel heterogeneous Pd−catalyst system (Pd-MNPSS) was developed using immobilization of Pd species (Pd II and Pd 0 ) on starch-functionalized magnetic nanoparticles. For the synthesis of Pd-MNPSS catalyst, first, magnetic nanoparticles (MNPs) were prepared and coated with a silica layer (Fe 3 O 4 @SiO 2 ) to increase their stability and functionalization capability. The Fe 3 O 4 @SiO 2 particles were reacted with thionyl chloride (SOCl 2 ) to generate chlorosilyl groups on the surface of MNPs. Reaction of starch with chloro-functionalized MNPs leads to a magnetic reusable polyhydroxy-functionalized substrate (MNPSS), which is highly suitable for immobilization of Pd metal on its surface. This catalyst system was designed to be applied in Pd-catalyzed organic coupling reactions in water. Finally, the Pd-MNPSS catalyst was prepared via reaction of MNPSS and Pd(OAc) 2 . After characterization of the Pd-MNPSS catalyst it was applied in the Heck and Sonogashira coupling reactions in water solvent, and excellent results were obtained. The catalyst system was separated from the reaction mixture employing an outside magnetic field. In these processes the catalyst was reusable for 5 times without remarkable decrease in its activity. The Pd-MNPSS catalyst has many advantages especially in the workup process related to our previously reported catalyst systems, Pd supported on silica−starch substrate (PNP-SSS) and Pd supported on silica− cyclodextrin substrate (PNP-SCD).

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Supported Palladium on Magnetic Nanoparticles–Starch Substrate (Pd-MNPSS): Highly Efficient Magnetic Reusable Catalyst for C–C Coupling Reactions in Water

Tukhani

Panahi

Khalafi-Nezhad

2017

ACS Sustainable Chem. Eng.

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“…Copper and its salts exhibit broad catalytic activity mainly due to the easily accessible and reasonable stability of Cu(0), Cu(I), Cu(II) and Cu(III) oxidation states. They are therefore effective catalysts not only for C arom -H bonds transformations by single electron transfer (SET) processes [1,2] but through using appropriate conditions even for C aromhalogen cleavage reactions by SET, two-electron transfer, or other mechanisms [3,4]. Copper also ranks among the cheap, earth-abundant first-row transition metals which are more environmentally acceptable (relatively less toxic) metals in comparison with noble platinum group metals, gold or silver.…”

Section: Introductionmentioning

confidence: 99%

The Influence of Copper on Halogenation/Dehalogenation Reactions of Aromatic Compounds and Its Role in the Destruction of Polyhalogenated Aromatic Contaminants

Weidlich

2021

Catalysts

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The effect of copper and its compounds on halogenation and dehalogenation of aromatic compounds will be discussed in the proposed article. Cu oxidized to appropriate halides is an effective halogenation catalyst not only for the synthesis of halogenated benzenes or their derivatives as desired organic fine chemicals, but is also an effective catalyst for the undesirable formation of thermodynamically stable and very toxic polychlorinated and polybrominated aromatic compounds such as polychlorinated biphenyls, dibenzo-p-dioxins and dibenzofurans accompanied incineration of waste contaminated with halogenated compounds or even inorganic halides. With appropriate change in reaction conditions, copper and its alloys or oxides are also able to effectively catalyze dehalogenation reactions, as will be presented in this review.

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“…11−13 Also, monosaccharides stabilize the catalysts through chelation thereby promoting the catalytic cycle and thus preventing the deactivation of the active metal. 10 Several groups showcased the use of a monosaccharide−metal combination strategy for various reactions, such as cross-coupling, 14−17 Ullmann reactions, 18 multi component reactions, 19−22 click reaction, 23,24 and domino reactions. 25 Of all of the several monosaccharides that are explored in these applications, glucose is most widely used due to its inexpensiveness, natural availability, and ability to reduce many metals very efficiently into a colloidal form.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In this context, from a sustainability point of view, the use of monosaccharides to assist in situ formation of low valent metals for cross-coupling reactions, particularly using cheap copper salts, has drawn significant interest due to its several benefits. Monosaccharides are eco-friendly, biorenewable, and are good cost-effective alternatives to generate in situ low-valent metal species when compared to other reducing agents, such as TBAX salts, tetrakis(dimethylamino)ethylene (TDAE), and others, in metal-mediated cross-coupling reactions. − Also, monosaccharides stabilize the catalysts through chelation thereby promoting the catalytic cycle and thus preventing the deactivation of the active metal . Several groups showcased the use of a monosaccharide–metal combination strategy for various reactions, such as cross-coupling, − Ullmann reactions, multi component reactions, − click reaction, , and domino reactions .…”

Section: Introductionmentioning

confidence: 99%

Cu(II)–Glucose: Sustainable Catalyst for the Synthesis of Quinazolinones in a Biomass-Derived Solvent 2-MethylTHF and Application for the Synthesis of Diproqualone

Dubey

Kumar

2018

ACS Sustainable Chem. Eng.

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An efficient method for the synthesis of quinazolinones by a domino cross-coupling reaction of 2-halobenzoic acids and amidines is demonstrated for the first time using a copper–glucose combination as an inexpensive catalytic system in a biomass-derived green solvent 2-methylTHF. Here, glucose plays a dual role, both as a reducing agent generating the low-valent copper ions from cupric precursors and as a chelating agent of the generated low-valent copper species, thereby impeding their deactivation. A wide variety of quinazolinones were synthesized in good to excellent yields. Notably, the activation of less reactive 2-bromo/chlorobenzoic acids by the catalyst not only advocates the efficiency of the developed protocol but also the broad substrate scope. Moreover, the developed methodology was successfully applied to the synthesis of the drug molecule diproqualone. The UV–vis spectrophotometric titration study of cupric and cuprous salts with glucose showed evidence of glucose playing the role as a ligand, thus it may act as a stabilizing agent for the low valent copper species formed in the reaction. The use of inexpensive and air stable cupric salts along with glucose for the synthesis of quinazolinones in a green solvent makes this a benign and sustainable method.

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Use of Monosaccharides in Metal-Catalyzed Coupling Reactions

Abstract: The addition of monosaccharides to metal- were observed for aryl iodides 3 bearing electron-withdrawing

Cited by 10 publications

References 90 publications

Supported Palladium on Magnetic Nanoparticles–Starch Substrate (Pd-MNPSS): Highly Efficient Magnetic Reusable Catalyst for C–C Coupling Reactions in Water

Supported Palladium on Magnetic Nanoparticles–Starch Substrate (Pd-MNPSS): Highly Efficient Magnetic Reusable Catalyst for C–C Coupling Reactions in Water

The Influence of Copper on Halogenation/Dehalogenation Reactions of Aromatic Compounds and Its Role in the Destruction of Polyhalogenated Aromatic Contaminants

Cu(II)–Glucose: Sustainable Catalyst for the Synthesis of Quinazolinones in a Biomass-Derived Solvent 2-MethylTHF and Application for the Synthesis of Diproqualone

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