Synthesis of PEG-supported organotrifluoroborates and their applications in palladium-catalyzed homo-coupling reactions

Carbon–carbon and carbon–heteroatom coupling reactions are among the most important transformations in organic synthesis as they enable complex structures to be formed from readily available compounds under different routes and conditions. Several metal-catalyzed cross-coupling reactions have been developed creating many efficient methods accessible for the direct formation of new bonds between differently hybridized carbon atoms.During the last decade, much effort has been devoted towards improvement of the sustainability of these reactions, such as catalyst recovery and atom efficiency. Polyethylene glycol (PEG) can be used as a medium, as solid-liquid phase transfer catalyst, or even as a polymer support. PEG has been investigated in a wide variety of cross-coupling reactions either as an alternative solvent to the common organic solvents or as a support for catalyst, substrate, and ligand. In this review we will summarize the different roles of PEG in palladium- and copper-catalyzed cross-coupling reactions, with the focus on Heck, Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Stille, Fukuyama, and homocoupling reactions. We will highlight the role of PEG, the preparation of PEGylated catalysts and substrates, and the importance for the reaction outcome and applicability.1 Introduction2 PEG in Heck Reactions3 PEG in Homocoupling Reactions4 PEG in Suzuki–Miyaura Reactions5 PEG in Sonogashira Reactions6 PEG in Buchwald–Hartwig Reactions7 PEG in Stille Reactions8 PEG in Fukuyama Reactions9 PEG in Miscellaneous Cross-Coupling Routes10 Conclusions

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The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions

Pires

Purificação

Santos

et al. 2017

Synthesis

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An Overview of Solid Supported Palladium and Nickel Catalysts for C-C Cross Coupling Reactions

Chopra

Ajay

Baroliya

2020

MROC

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Solid supported catalysts have been of considerable interest in organic synthesis for last few years. Solid support provides an efficient heterogeneous catalytic system owing to facile recovery and extensive recycling by simple filtration because of possessing 3-R approach (Recoverable, Robust and Recyclable) and makes solid supported catalyst more appealing nowadays. In view of the high cost and shortage of furthermost used palladium catalyst, its recovery and recycling are vital issues for any large-scale application which are being overcome by using solid supported catalytic systems. Therefore, a variety of inorganic and organic solid-supported catalytic systems have been developed so far in order to address these challenges. This review attempts highlight a number of solid supported catalytic systems in the pro-active area of widely used C−C cross coupling reactions.

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Synthesis of PEG-supported organotrifluoroborates and their applications in palladium-catalyzed homo-coupling reactions

Cited by 2 publications

References 32 publications

The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions

The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions

An Overview of Solid Supported Palladium and Nickel Catalysts for C-C Cross Coupling Reactions

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