Highly-efficient and recyclable nanosized MCM-41 anchored palladium bipyridyl complex-catalyzed coupling of acyl chlorides and terminal alkynes for the formation of ynones

Chen, Jun-You; Lin, Tze-Chiao; Chen, Szu-Chien; Chen, Ai-Jan; Mou, Chung‐Yuan; Tsai, Fu‐Yu

doi:10.1016/j.tet.2009.10.031

Cited by 38 publications

(19 citation statements)

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“…Although most known heterogeneous catalysts have been demonstrated to be able to be recycled for use in further runs, the use of catalytic amounts of 0.2–5 mol% of Pd for the Sonagashira reaction is still too high for a single batch reaction when compared with homogeneous catalysts [ 49 , 50 , 51 , 52 , 53 , 54 ]. We have recently prepared a nanosized MCM-41 grafted palladium bipyridyl complex, NS-MCM-41-Pd ( Figure 1 ), as a highly efficient and recyclable catalyst for the Mizoroki-Heck reaction [ 55 ], Kumada-Tamao-Corriu reaction [ 56 ], ketone formation [ 57 ], and ynone formation [ 58 ], which require a very low catalyst loading for a single batch reaction.…”

Section: Introductionmentioning

confidence: 99%

Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex

Lin

Huang

et al. 2010

Molecules

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A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using low Pd loadings to 0.01 mol%, and the nanosized MCM-41-Pd catalyst was recovered by centrifugation of the reaction solution and re-used in further runs without significant loss of reactivity.

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Section: Introductionmentioning

confidence: 99%

Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex

Lin

Huang

et al. 2010

Molecules

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“…Tsai et al [40,41] studied a highly-efficient and recyclable MCM-41 anchored palladium bipyridyl complex-catalyzed ( Figure 29). The MCM-41 were prepared by grafting of the palladium bipyridyl complex onto pristine MCM-41.…”

Section: Catalysts 2018 8 X For Peer Review 14 Of 63mentioning

confidence: 99%

Functionalized Ordered Mesoporous Silicas (MCM-41): Synthesis and Applications in Catalysis

et al. 2018

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Mesoporous silica sieves are among the most studied nano-objects due to their stable pore structure and easy preparation. In particular, MCM-41 have attracted increasing research attention due to their chemical versatility. This review focuses on the synthesis and regioselective functionalization of MCM-41 to prepare catalytic systems. The topics covered are: mono and di-functionalized MCM-41 as basic and acid catalysts, catalysts based on metallic complexes and heteropolyacids supported onto MCM-41, metallic nanoparticles embed onto functionalized MCM-41 and magnetic MCM-41 for catalytic purposes.

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“…Another anchored catalyst ( Figure 6) was prepared by Tsai's group [50] and used in the formation of ynones via Sonogashira reaction of aroyl, heteroaroyl and alkyl acyl chlorides and terminal alkynes. A bipyridyl palladium complex was linked to a mesoporous silica material MCM-41 and employed in very low amount, 0.02 mol %; nevertheless, optimized reaction conditions required Et 3 N as the base and the solvent, CuI and triphenylphosphine.…”

Section: Palladium Supported Catalysts For Acyl Sonogashira Reactionsmentioning

confidence: 99%

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

Albano

Aronica

2019

Catalysts

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The acyl Sonogashira reaction represents an extension of Sonogashira cross-coupling to acid chlorides which replace aryl or vinyl halides, while terminal acetylenes are used as coupling partners in both reactions. The introduction of a carbonyl functional group on the alkyne backbone determines a radical change in the reactivity of the products. Indeed, α,β-alkynyl ketones can be easily converted into different heterocyclic compounds depending on the experimental conditions employed. Due to its potential, the acyl Sonogashira reaction has been deeply studied with particular attention to the nature of the catalysts and to the structures of both coupling compounds. Considering these two aspects, in this review, a detailed analysis of the literature data regarding the acyl Sonogashira reaction and its role in the synthesis of several heterocyclic derivatives is reported.

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Highly-efficient and recyclable nanosized MCM-41 anchored palladium bipyridyl complex-catalyzed coupling of acyl chlorides and terminal alkynes for the formation of ynones

Cited by 38 publications

References 70 publications

Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex

Sonogashira Reaction of Aryl and Heteroaryl Halides with Terminal Alkynes Catalyzed by a Highly Efficient and Recyclable Nanosized MCM-41 Anchored Palladium Bipyridyl Complex

Functionalized Ordered Mesoporous Silicas (MCM-41): Synthesis and Applications in Catalysis

Acyl Sonogashira Cross-Coupling: State of the Art and Application to the Synthesis of Heterocyclic Compounds

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