Nucleophilic substitution reactions of allylic esters catalysed by palladium-graphite and related heterogeneous catalysts

Boldrini, Gian Paolo; Savoia, Diego; Tagliavini, Emilio; Trombini, Claudio; Umani‐Ronchi, Achille

doi:10.1016/0022-328x(84)85102-5

Cited by 33 publications

(7 citation statements)

References 46 publications

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“…Boldrini and co-workers reported a Pd/C-catalyzed allylation using allyl acetate (Trost-Tsuji reaction) (Scheme 33). 82 They were successful in achieving the allylation of sodium benzenesulfinate 70, though the yield was inferior to that obtained with homogeneous palladium(II) chloride. Roth and co-workers at Boehringer Ingelheim found that the Stille coupling of iodonitrobenzene 72 with thienylstannane 73 took place using Pd/C as the catalyst (Scheme 34).…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Recent Advances in Pd/C-Catalyzed Coupling Reactions

Shimada¹

2006

Synthesis

182

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A practical approach to multifunctional compounds through palladium on activated carbon (Pd/C)-catalyzed coupling reactions is described. A close correlation of the properties of the Pd/C with reaction efficiency has been observed and depends largely upon the type of reaction. A critical role of the activated carbon is to help palladium disperse sufficiently on the solid support to form the active palladium complex without aggregating to inactive palladium black. The use of Pd/C avoids contamination of the product with palladium and expedites recovery of the metal. The reactions are practical and have been applied to cost-effective largescale production of multifunctional compounds for drug synthesis. 4 Reaction Mechanism 5 Conclusion

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Recent Advances in Pd/C-Catalyzed Coupling Reactions

Shimada¹

2006

Synthesis

182

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“…12 Palladium graphite can also be employed as a heterogeneous catalyst in the above reaction. 13 Utilizing Pd(PPh 3 ) 4 catalysis, allyl acetate or phenoxide reacts with various hexanone enamines to give 2-allylcyclohexanone in moderate yields. 14 Under neutral conditions, ketones and aldehydes react with 2-allylisourea in the presence of a catalytic amount of a palladium(0) complex to give γ,δ-unsaturated ketones and aldehydes.…”

Section: Introductionmentioning

confidence: 99%

Palladium(0)-Catalyzed Reactions of Allylic Benzotriazoles with Enamines: A Novel Method for the Stereoselective Synthesis of (4E)-γ,δ-Unsaturated Ketones

1999

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“…13 Palladium-graphite (Pd-Gr) which is prepared by the metal exchange reaction of potassium-intercalated graphite showed a high reactivity for the hydrogenation of olefins,14 the Heck reaction,15 and the nucleophilic substitution reactions through the .i-allyl complex. 16 This paper describes the first investigation of polycondensation using the Pd-Gr-catalyzed Heck reaction.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Polycinnamamide Catalyzed by Palladium-Graphite through the Heck Reaction

Jikei¹,

Ishida²,

Seo³

et al. 1995

Macromolecules

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Palladium-graphite (Pd-Gr) was successfully used as a heterogeneous catalyst for the preparation of polycinnamamide through the Heck reaction. The condensation reaction of ethyl acrylate and iodobenzene catalyzed by Pd-Gr proceeded efficiently in the presence of tributylamine in an aprotic polar solvent such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methylpyrrolidone (NMP), and dimethyl sulfoxide (DMSO). The polymerization of N,N'-(3,4'-oxydiphenylene)bis-(acrylamide) and bis(4-iodophenyl) ether catalyzed by Pd-Gr was carried out in the presence of tributylamine in DMF a t 100 "C. The polymerization proceeded efficiently to form polycinnamamide, but required a longer reaction time compared to the polycondensation catalyzed by palladium acetate. The structure of the resulting polymer was confirmed as trans-polycinnamamide by two-dimensional NMR measurements. The resulting polymer was almost white, which means that it was less contaminated by palladium metal. The removal and recycling of Pd-Gr were much easier than in the case of homogeneous catalysts.

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Nucleophilic substitution reactions of allylic esters catalysed by palladium-graphite and related heterogeneous catalysts

Cited by 33 publications

References 46 publications

Recent Advances in Pd/C-Catalyzed Coupling Reactions

Recent Advances in Pd/C-Catalyzed Coupling Reactions

Palladium(0)-Catalyzed Reactions of Allylic Benzotriazoles with Enamines: A Novel Method for the Stereoselective Synthesis of (4E)-γ,δ-Unsaturated Ketones

Preparation of Polycinnamamide Catalyzed by Palladium-Graphite through the Heck Reaction

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