Heterogeneous Heck reaction catalyzed by Pd/C in ionic liquid

Hagiwara, Hisahiro; Shimizu, Yumiko; Hoshi, Takashi; Suzuki, Toshio; Ando, Masayoshi; Ohkubo, K.; Yokoyama, Chiaki

doi:10.1016/s0040-4039(01)00748-1

Cited by 147 publications

(64 citation statements)

References 23 publications

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“…Accordingly, the search for recoverable supported catalysts has received much attention in recent years. 11 -19 Palladium catalysts supported on polymer, 18 activated carbon, 20 metal oxides 21 and zeolites 22 have been developed to overcome typical problems such as separation and recycling in homogeneous catalysis. However, traditional heterogeneous catalysts are rather limited in the nature of their active sites, and thus these systems do not achieve the excellent activities observed with homogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Fan

Cheng

Zhu

et al. 2007

Applied Organom Chemis

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Palladium chloride was grafted to amino-functionalized MCM-41 to prepare heterogeneous catalysts. XRD, N 2 adsorption-desorption isotherms, IR, 13 C and 29 Si cross-polarization magic-angle spinning NMR spectroscopy and XPS techniques were employed to characterize the catalytic materials. The heterogeneous palladium catalyst exhibited excellent catalytic activity for the Heck vinylation of iodobenzene with methyl acrylate, giving 92% yield of methyl cinnamate in the presence of Nmethylpyrrolidone (NMP) and triethylamine (Et 3 N). The stability of the heterogeneous catalyst was also studied in detail. The catalytic tests showed that the palladium leaching correlated to solvent, base and palladium loading. The heterogeneous catalyst exhibited excellent stability towards loss of activity and palladium leaching was not observed during six recycles in the presence of toluene and Na 2 CO 3 .

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Section: Introductionmentioning

confidence: 99%

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Fan

Cheng

Zhu

et al. 2007

Applied Organom Chemis

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“…The rate enhancements may derive from a solvent-effect such as the one observed for the same reaction carried out in the ionic liquid [bmim]PF 6 with Pd/C. 18 What appears important is the interaction of A336 with the supported metal catalyst, as well as its ability to mediate mass transfer between the catalyst and the bulk solution. These effects appear responsible for the changes in rates and selectivity observed in the present case.…”

Section: Discussionmentioning

confidence: 98%

“…17 The Heck reaction between aryl iodides and activated olefins was reported in the ionic liquid [bmim]PF 6 with a Pd/C catalyst as well. 18 Jeffery also noted that the Heck reaction was favoured by phase transfer catalysts (PTC), such as quaternary ammonium salts. 19,20 It therefore appears that the Heck reaction benefits from the presence of a PTC, either in the form of a PTC or of an ionic liquid.…”

Section: Homogeneous Catalyst Immobilized In Ionic Liquidsmentioning

confidence: 99%

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Heck reaction catalyzed by Pd/C, in a triphasic—organic/Aliquat 336/aqueous—solvent system

et al. 2004

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The rate of the Pd/C catalyzed Heck coupling of Ar-I with CH 2 CH-R is accelerated tenfold by the presence of Aliquat 336 (A336), a well known phase transfer catalyst, and an ionic liquid. Both when conducted in A336 as solvent, and in an isooctane/A336/aqueous triphasic mixture, the Heck reaction of aryl iodides with electron deficient olefins, catalyzed by Pd/C, proceeds with high yields and selectivity. When KOH is used instead of Et 3 N, selective formation of the biphenyl rather than the Heck product, is observed. Aryl bromides react more sluggishly, and only the more activated ones undergo the Heck reaction. In the absence of the olefin, aryl halides possessing an electron withdrawing group are reduced to the corresponding Ar-H.

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“…When methyl vinyl ketone (82b) was used instead of 82a, the chemical yield of the 1st run was 76%, [142][143][144][145][146][147][148] and almost the same chemical yield continued through 10 runs.…”

Section: Development Of Palladium Catalyst Supported On Gaas(001): Bmentioning

confidence: 99%

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

Arisawa

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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We have developed a novel organometallic catalysis and applied it to drug discovery. Two new catalysts were found, ruthenium hydride with a nitrogen-containing heterocyclic carbene (A) and an organopalladium catalyst supported on a sulfur-terminated semiconductor, gallium arsenide (001) (B). Both catalysts are environmentally benign, because A can yield indole derivatives with good atom economy, and B can catalyze the Mizoroki-Heck reaction more than 10 times with only trace amounts of leached palladium (ppb level). We also describe our synthetic study of nitrogen-containing heterocycles using ring-closing metathesis (RCM), such as chiral bicyclic lactams, azacycloundecenes, axially chiral macrolactams, 1,2-dihydroquinolines and indoles, including the development of silyl-enol ether ene metathesis, selective isomerization of terminal olefin, enamide metathesis and cycloisomerization and its application to the syntheis of 4 natural products, (؊)-coniceine, (S)-pyrrolam A, angustureine, and fistulosin.

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Heterogeneous Heck reaction catalyzed by Pd/C in ionic liquid

Cited by 147 publications

References 23 publications

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Heck reaction catalyzed by Pd/C, in a triphasic—organic/Aliquat 336/aqueous—solvent system

Development of Environmentally Benign Organometallic Catalysis for Drug Discovery and Its Application

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