PEG Click‐Triazole Palladacycle: An Efficient Precatalyst for Palladium‐Catalyzed Suzuki‐Miyaura and Copper‐free Sonogashira Reactions in Neat Water

Zhang, Guofu; Zhang, Wei; Luan, Yu‐Xin; Han, Xingwang; Ding, Chengrong

doi:10.1002/cjoc.201500167

Cited by 17 publications

(6 citation statements)

References 91 publications

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“…Various N-donor ligands have been reported, including pyridines, imines, imidates, pyrimidines, amines, palladacycles, amides, and others (Scheme ). − …”

Section: Metal-based Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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Traditional organic synthesis relies heavily on organic solvents for a multitude of tasks, including dissolving the components and facilitating chemical reactions, because many reagents and reactive species are incompatible or immiscible with water. Given that they are used in vast quantities as compared to reactants, solvents have been the focus of environmental concerns. Along with reducing the environmental impact of organic synthesis, the use of water as a reaction medium also benefits chemical processes by simplifying operations, allowing mild reaction conditions, and sometimes delivering unforeseen reactivities and selectivities. After the "watershed" in organic synthesis revealed the importance of water, the development of water-compatible catalysts has flourished, triggering a quantum leap in water-centered organic synthesis. Given that organic compounds are typically practically insoluble in water, simple extractive workup can readily separate a water-soluble homogeneous catalyst as an aqueous solution from a product that is soluble in organic solvents. In contrast, the use of heterogeneous catalysts facilitates catalyst recycling by allowing simple centrifugation and filtration methods to be used. This Review addresses advances over the past decade in catalytic reactions using water as a reaction medium.

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“…Various N-donor ligands have been reported, including pyridines, imines, imidates, pyrimidines, amines, palladacycles, amides, and others (Scheme ). − …”

Section: Metal-based Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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“…In 2015, the same group described a PEG‐triazole‐carbene dimeric pallasium complex that promoted the Suzuki–Miyaura cross‐coupling of aryl iodides or bromides with phenylboronic acid at a catalyst loading of 500 mol ppb (Scheme ) . Twenty‐four examples at that loading gave at least 90% yield.…”

Section: Suzuki–miyaura Cross‐couplingmentioning

confidence: 99%

Recent Advances in Palladium‐Catalyzed Cross‐Coupling Reactions at ppm to ppb Molar Catalyst Loadings

2017

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We review here new developments in decreasing the catalyst loadings in palladium-catalyzed C-C bond-formation reactions to mol ppm or mol ppb levels.T his decreasest he cost of the catalyst and the toxicity of the reactions ystem, making the reactionm ore attractive to industry.T he Heck reaction, Sonogashira reaction, Suzuki-Miyaurac rosscoupling reaction, other cross-coupling reactions,a nd allylic arylation reactions are separately discussedt o show clearly the progress made in each type of reaction. Apart from the catalyst loading, the other parameters of the reaction( temperature,s olvent, etc.) are brieflyd iscussed to illustrate the shift toward greenerc onditions.F or most reactions,t his shift is underway or wella dvanced, andc atalyst loadings have been decreasedt ob elow 1mol ppm. An abundance of catalytic systems are now available,a nd it is sometimes difficult to identify the best one,b ecause the substratese xamined can vary widely from publication to publication.I nt he future,e mphasis should be placed on the studyingt he full scope of the reaction at mol ppm catalyst loadings,r athert han examining af ew examples at these levels during the reaction-optimization process.1I ntroduction 2M izoroki-Heck Coupling 3S onogashira Coupling 4S uzuki-MiyauraCross-Coupling 5O ther Cross-Coupling Reactions 6A llylic Arylation 7C onclusions

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“…Palladacycles are interesting because they are believed to release highly active Pd(0) species at a very slow rate, which prevents the deactivation of Pd(0) such as nanoparticle formation, thus achieving high turnover numbers. Palladacycles are Scheme 20 SMC in water with an orthometallated aryltriazole palladium complex bearing a PEG solubilizing unit [38]. formed by C-H activation of aromatic moiety near a coordination site in the ligand.…”

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confidence: 99%

“…formed by C-H activation of aromatic moiety near a coordination site in the ligand. A novel water-soluble palladacycle 32 has been reported by Ding (Scheme 20) [38]. The catalyst exhibited superior catalytic activity towards the SMC in neat water with TONs of up to 9.8×105 .…”

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confidence: 99%

Recent Advances in the Palladium Catalyzed Suzuki–Miyaura Cross-Coupling Reaction in Water

2016

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The palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of organic halides with boronic acids is one of the most versatile methods for the synthesis of biaryls. Green chemistry is a rapidly developing new field that provides us a proactive avenue for the sustainable development of future science and technologies. When designed properly, clean chemical technology can be developed in water as a reaction medium. The technologies generated from such green chemistry endeavors may often be cheaper and more profitable. This review covers the literature on palladium-catalysed the Suzuki-Miyaura cross-coupling reaction in water.

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PEG Click‐Triazole Palladacycle: An Efficient Precatalyst for Palladium‐Catalyzed Suzuki‐Miyaura and Copper‐free Sonogashira Reactions in Neat Water

Abstract: The employed catalyst can be reused at least three times without significant loss of reactivity.

Cited by 17 publications

References 91 publications

Catalytic Organic Reactions in Water toward Sustainable Society

Catalytic Organic Reactions in Water toward Sustainable Society

Recent Advances in Palladium‐Catalyzed Cross‐Coupling Reactions at ppm to ppb Molar Catalyst Loadings

Recent Advances in the Palladium Catalyzed Suzuki–Miyaura Cross-Coupling Reaction in Water

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