Anatomy of high recyclability of graphene oxide based palladium nanocomposites in the Sonogashira reaction: On the nature of the catalyst deactivation

Kim, Bo‐Hyun; Lee, Soul-Hee; Han, Sang-Wook; Ahn, Seokhoon; Noh, Jaegeun; Park, Joon B.

doi:10.1166/mex.2016.1280

Cited by 13 publications

(9 citation statements)

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“…In addition, the reaction conditions involve the use of copper as cocatalysts and triphenylphosphine as ligand, which reduce the interest of this catalytic system. Moreover, PdNPs supported on other carbon-derived materials, such as partially reduced graphene oxide (PdNPs@PRGO, 23) [53], reduced graphene oxide (PdNPs@RGO, 24) [54], graphene oxide (PdNPs@GO, 25) [54,55], and nanoporous carbon hollow tubes (PdNPs@CHT, 26) [56] have …”

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

“…Moreover, PdNPs supported on other carbon-derived materials, such as partially reduced graphene oxide (PdNPs@PRGO, 23) [53], reduced graphene oxide (PdNPs@RGO, 24) [54], graphene oxide (PdNPs@GO, 25) [54,55], and nanoporous carbon hollow tubes (PdNPs@CHT, 26) [56] have generally shown good activity in the Sonogashira reaction of aryl halides ( Figure 9). Usually, these supported catalyst are easily deactivated after several reaction cycles [54]. Regardless of the carbon-derived material employed as support, the stability and catalytic activity of supported PdNPs in the Sonogashira coupling can be improved following different strategies.…”

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

“…Regarding recyclability, only a minor decrease of the reaction yield was observed after six reaction cycles for the coupling between phenyl iodide and phenylacetylene (99% to 93%). Usually, these supported catalyst are easily deactivated after several reaction cycles [54]. Regardless of the carbon-derived material employed as support, the stability and catalytic activity of supported PdNPs in the Sonogashira coupling can be improved following different strategies.…”

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

“…In this case, the gold acts as stabilizing agent for the Pd(0) species, allowing the conservation of the PdNP morphology [bimodal distribution containing small NPs (10-15 nm) along with aggregated particles (100 nm)] and thus the catalytic activity of the system, which shows good functional group tolerance and excellent reactivity for aliphatic acetylenes. Usually, these supported catalyst are easily deactivated after several reaction cycles [54]. Regardless of the carbon-derived material employed as support, the stability and catalytic activity of supported PdNPs in the Sonogashira coupling can be improved following different strategies.…”

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

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Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

et al. 2018

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Abstract:The Sonogashira cross-coupling reaction is the most frequently employed synthetic procedure for the preparation of arylated alkynes, which are important conjugated compounds with multiple applications. Despite of their rather high price, this reaction is usually catalyzed by palladium species, making the recovery and reuse of the catalyst an interesting topic, mainly for industrial purposes. Easy recycle can be achieved anchoring the palladium catalyst to a separable support. This review shows recent developments in the use of palladium species anchored to different solid supports as recoverable catalysts for Sonogashira cross-coupling reactions.

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Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

Section: Carbon-based Material-supported Palladium Catalystsmentioning

confidence: 99%

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Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

et al. 2018

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“…Recently, Ahn and co‐workers published the preparation of the Pd NPs dispersed on both reduced graphene oxide (Pd/RGO) and graphene oxide (Pd/GO) and also demonstrated their application as novel catalysts for the Sonogashira coupling reactions (Scheme ) . Figure shows TEM images of the as‐prepared Pd/GO and Pd/RGO and recycled Pd/GO and Pd/RGO.…”

Section: C−c and C−x Coupling Reactions Catalyzed By Graphene Supportmentioning

confidence: 99%

Recent Progress in Application of Graphene Supported Metal Nanoparticles in C−C and C−X Coupling Reactions

Nasrollahzadeh

Issaabadi

Tohidi

et al. 2017

The Chemical Record

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The carbon-carbon and carbon-heteroatom bonds catalytic formation is among the most significant reactions in organic synthesis which extensively applied for synthesis of natural products, heterocycles, dendrimers, biologically active molecules and useful compounds. This review provides the latest advances in the preparation of graphene supported metal nanoparticles and their application in the catalytic formation of both carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds including the Suzuki, Heck, Hiyama, Ullmann, Buchwald and Sonogashira coupling reactions. Numerous examples are given concerning the use of these catalysts in C-C and C-X coupling reactions along with the reliable and simple preparation methods of these catalysts, their characterization and catalytic properties and also the recycling possibilities.

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Recent Advances in Graphene and Graphene‐Based Heterogeneous Nanocatalysts: C−C And C−Y Coupling Reactions in Liquid Phase

Paunkumar

Babu

2022

ChemistrySelect

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Up to date, graphene has been widely used in organic transformations as a supporting material due to its superior physical and chemical properties as well as being cost‐effective. Metal nanocomposite as a catalyst has been studied in the formation of carbon‐carbon and carbon‐heteroatom bonds formation reactions such as Suzuki, Ullmann, Heck, Sonogashira, C−O, C−N, and C−S cross‐coupling reactions. The efficient catalysts were characterized by analytical and microscopic techniques and investigated their reusability. The reactions gave the desired products (pharmaceutical intermediate products) an easier path. This review mainly focuses on metal nanoparticles supported by graphene derivatives towards the C−C and C−Y (Y=O, S, N) cross‐coupling reactions in liquid phase heterogeneous catalysis.

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Anatomy of high recyclability of graphene oxide based palladium nanocomposites in the Sonogashira reaction: On the nature of the catalyst deactivation

Cited by 13 publications

References 0 publications

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

Recent Progress in Application of Graphene Supported Metal Nanoparticles in C−C and C−X Coupling Reactions

Recent Advances in Graphene and Graphene‐Based Heterogeneous Nanocatalysts: C−C And C−Y Coupling Reactions in Liquid Phase

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