On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homogeneous or Heterogeneous Catalysis, A Critical Review

Phan, Nam T. S.; Sluys, Matthew Van Der; Jones, Christopher W.

doi:10.1002/adsc.200505473

Cited by 1,840 publications

(1,247 citation statements)

References 572 publications

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“…Some important physicochemical parameters such as polarity are still under debate and others, like their distillation process, is so-far indisputable. The importance of carbenes as active catalytic species have been already reported, [61][62][63] especially those derived of 1,3-dialkylimidazolium cation. [63][64][65][66][67] Even though, there are many challenges surrounding the carbene chemistry and its potential applications in the field of organo-and organometallic catalysis.…”

Section: Discussionmentioning

confidence: 99%

The impressive chemistry, applications and features of ionic liquids: properties, catalysis & catalysts and trends

Neto¹,

Spencer²

2012

J. Braz. Chem. Soc.

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Algumas das nossas contribuições para o desenvolvimento da área da catálise em líquidos iônicos são descritas. Além disto, o uso de ligantes ionofílicos bem como a utilização de catalisadores com "etiquetas iônicas" são apresentados e discutidos. Devido à importância dos líquidos iônicos, as suas propriedades fisicoquímicas de interesse bem como a sua organização supramolecular são temas discutidos.Some of our contributions to the development of catalysis in ionic liquids are described. Also, the use of ionophilic ligands and catalysts with ionic tags are presented and discussed. Due to the importance of ionic liquids, some physicochemical properties of interest and their supramolecular organization are described.

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Section: Discussionmentioning

confidence: 99%

The impressive chemistry, applications and features of ionic liquids: properties, catalysis & catalysts and trends

Neto¹,

Spencer²

2012

J. Braz. Chem. Soc.

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“…The comparison of homogeneous and heterogeneous paths for the ligandless Mizoroki-Heck reactions are also overviewed [78]. The role of Pd in coupling reactions has been taken into account by critically assessing the role of the "heterogeneous" vs. "homogeneous" species playing a role in the reaction [79]. The life of heterogeneous Pd catalysts has been also considered by Reynolds et al [80] demonstrating negligible leaching.…”

Section: Methodsmentioning

confidence: 99%

Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

Rossetti

Compagnoni

2016

Chemical Engineering Journal

198

103

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Flow chemistry has been proposed in modern organic chemistry as a mean for process intensification, to improve the control over reaction performance and to achieve higher yield. However, many open issues can be evidenced regarding the true possibility of scale-up, as well as currently lacking information for process design and economical evaluation. This review proposes some recent examples of flow synthesis deepening in particular the scale-up and engineering issues. Required information is evidenced, as well as some transport and kinetic data required for the practical implementation of the results.

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“…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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On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homogeneous or Heterogeneous Catalysis, A Critical Review

Cited by 1,840 publications

References 572 publications

The impressive chemistry, applications and features of ionic liquids: properties, catalysis & catalysts and trends

The impressive chemistry, applications and features of ionic liquids: properties, catalysis & catalysts and trends

Chemical reaction engineering, process design and scale-up issues at the frontier of synthesis: Flow chemistry

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

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