Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts

Yin, Lunxiang; Liebscher, Jürgen

doi:10.1021/cr0505674

Cited by 2,013 publications

(884 citation statements)

References 281 publications

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“…Among them are reactions that directly couple two different sp 2 -hybridized carbon centers to form an olefin (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). Conceptually, the simplest process would be the dimerization and cross-coupling of two free carbenes (Fig.…”

mentioning

confidence: 99%

Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes

Lavallo

Frey

Kousar

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

281

165

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mentioning

confidence: 99%

Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes

Lavallo

Frey

Kousar

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

281

165

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“…4 This explanation is supported by our own findings, as evidenced by 18 and 20. Interestingly, an indole N-H (pKa 35 16.97) was well tolerated (16,17).…”

Section: Resultsmentioning

confidence: 99%

“…With ligand-free catalytic systems, the reaction also becomes more environmentally friendly and the workup is further simplified. 15 Various supports for palladium have been explored 16,17 such as palladium on carbon 18 , metal-organic frameworks (MOF), 19,20 28 This catalyst has been used successfully in transfer hydrogenation of alkenes and Suzuki couplings with aryl halides, 29 in racemization of amines, 28 in aerobic oxidation of primary and secondary alcohols 30 and in selective transfer hydrogenation of nitroarenes to anilines. 31 Recently, both enzyme Candida Antarctica Lipase B and palladium nanoparticles were immobilized in MCF (in the same cavity) and used for dynamic kinetic resolution (DKR) amines.…”

Section: Introductionmentioning

confidence: 99%

A General Suzuki Cross-Coupling Reaction of Heteroaromatics Catalyzed by Nanopalladium on Amino-Functionalized Siliceous Mesocellular Foam

et al. 2014

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Suzuki-Miyaura cross-coupling reactions of heteroaromatics catalyzed by palladium supported in the cavities of amino-functionalized silicious mesocellular foam is presented.The nanopalladium catalyst effectively couples not only heteroaryl halides with boronic acids, but also heteroarylboronic acids, boronate esters, potassium trifluoroborates, MIDA boronates and triolborates, producing a wide range of heterobiaryls in good to excellent yields.Furthermore, the heterogenous palladium nanocatalyst can easily be removed from the reaction mixture by filtration and recycled several times with minimal loss in activity. This catalyst provides an alternative, environmentally friendly, low-leaching process for the preparation of heterobiaryls.

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“…That is, the transformable heterogeneous and homogeneous catalysis can be achieved with the fluorinated catalysts and CO 2 without using additional organic and fluorous solvents, which are both needed for fluorous biphasic catalytic reactions [34][35][36]. The potential of the present CO 2 pressure tunable heterogeneous/homogeneous catalytic reaction system has also been studied for Sonogashira reaction [11,37,38] of iodobenzene and phenylacetylene under similar conditions. It is important to note here that our catalytic reaction systems are free of phosphine ligands, fluorinated solvents, and, possibly, conventional organic solvents.…”

Section: Methodsmentioning

confidence: 94%

“…A simple Heck reaction [12][13][14][15] of iodobenzene and methyl acrylate has been selected as a test reaction. Recently it was indicated that the pressurization with CO 2 accelerated the rate of Heck reactions with a Pd-TPP (TPP: triphenylphosphine) complex catalyst for a few selected substrates although the reactions took place in homogeneous liquid phases and CO 2 was not a reactant [16].…”

Section: Methodsmentioning

confidence: 99%

Carbon dioxide pressure induced heterogeneous and homogeneous Heck and Sonogashira coupling reactions using fluorinated palladium complex catalysts

Akiyama

Meng

Fujita

et al. 2009

The Journal of Supercritical Fluids

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The Heck reaction of iodobenzene and methyl acrylate was investigated with CO 2 -philic Pd complex catalysts having fluorous ponytails and the organic base triethylamine (Et 3 N) in the presence of CO 2 under solventless conditions at 80 C. The catalysts are not soluble in the organic phase in the absence of CO 2 and the reaction occurs in a solid-liquid biphasic system. When the organic liquid mixture is pressurized by CO 2 , CO 2 is dissolved into the organic phase and this promotes the dissolution of the Pd complex catalysts. As a result, the Heck reaction occurs homogeneously in the organic phase, which enhances the rate of reaction. This positive effect of CO 2 pressurization competes with the negative effect that the reacting species are diluted by an increasing amount of CO 2 molecules dissolved. Thus, the maximum conversion appears at a CO 2 pressure of around 4 MPa under the present reaction conditions. The catalysts are separated in the solid granules by depressurization and are recyclable without loss of activity after washing with n-hexane and/or water. When the washing is made with hexane alone, the catalytic activity tends to increase on the repeated Heck reactions, probably due to the accumulation of such a base adduct as Et 3 NHI on the catalysts. When the washing is further made with water, however, the base adduct is taken off from the catalysts and they show similar activity levels in the repeated runs. The potential of CO 2 pressure tunable heterogeneous/homogeneous reaction system has also been investigated for Sonogashira reactions of iodobenzene and phenylacetylene under similar conditions.

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Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts

Cited by 2,013 publications

References 281 publications

Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes

Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes

A General Suzuki Cross-Coupling Reaction of Heteroaromatics Catalyzed by Nanopalladium on Amino-Functionalized Siliceous Mesocellular Foam

Carbon dioxide pressure induced heterogeneous and homogeneous Heck and Sonogashira coupling reactions using fluorinated palladium complex catalysts

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