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01.04.2013 | Original Paper

Palladium nano-particles supported on ethylenediamine-functionalized cellulose as a novel and efficient catalyst for the Heck and Sonogashira couplings in water

verfasst von: Sajjad Keshipour, Salman Shojaei, Ahmad Shaabani

Erschienen in: Cellulose | Ausgabe 2/2013

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Abstract

Palladium nano-particles supported on ethylenediamine-functionalized cellulose as a novel bio-supported catalyst were synthesized and characterized. The synthesized catalyst was found to be a highly efficient heterogeneous catalyst for the Heck and Sonogashira couplings in H₂O as a green solvent at 100 °C in very low loading of Pd. The catalyst could be easily recovered by simple filtration and reused for at least 4 cycles without losing its activity.

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Vorheriger Artikel Preparation of superhydrophobic electroconductive graphene-coated cotton cellulose

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Augustine RL, O’Leary ST (1995) Effect of the catalyst support on the regiochemistry of the heck arylation reaction. J Mol Catal A: Chem 95:277–285CrossRef

Beletskaya IP, Cheprakov AV (2000) The Heck reaction as a sharpening stone of palladium catalysis. Chem Rev 100:3009–3066CrossRef

Belier M, Fischer H, Kiihlein K, Reisinger CP, Herrmarm WA (1996) First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems. J Organometal Chem 520:257–259CrossRef

Berthiol F, Doucet H, Santelli M (2005) Heck reaction of protected allyl alcohols with aryl bromides catalyzed by a tetraphosphine palladium complex. Eur J Org Chem 7:1367–1377CrossRef

Bhanage BM, Shirai M, Arai M (1999) Heterogeneous catalyst system for Heck reaction using supported ethylene glycol phase Pd/TPPTS catalyst with inorganic base. J Mol Catal A Chem 145:69–74CrossRef

Bhattacharya S, Sengupta S (2004) Palladium catalyzed alkynylation of aryl halides (Sonogashira reaction) in water. Tetrahedron Lett 45:8733–8736CrossRef

Bianco A, Cavarischia C, Guiso M (2004) The Heck coupling reaction using aryl vinyl ketones: synthesis of flavonoids. Eur J Org Chem 13:2894–2898CrossRef

Chen SL, Huang XJ, Xu ZK (2011) Functionalization of cellulose nanofiber mats with phthalocyanine for decoloration of reactive dye wastewater. Cellulose 18:1295–1303CrossRef

Chen SL, Huang XJ, Xu ZK (2012) Effect of a spacer on phthalocyanine functionalized cellulose nanofiber mats for decolorizing reactive dye wastewater. Cellulose 19:1351–1359CrossRef

Chinchilla R, Nájera C (2007) The Sonogashira reaction: a booming methodology in synthetic organic chemistry. Chem Rev 107:874–922CrossRef

Chinchilla R, Nájera C (2011) Recent advances in Sonogashira reactions. Chem Soc Rev 40:5084–5121CrossRef

Choudary BM, Sarma RM, Rao KK (1992) A highly active and stereoselective montmorillonite catalyst for arylation of conjugated alkenes. Tetrahedron 48:719–726CrossRef

Cirtiu CM, Dunlop-Briere AF, Moores A (2011) Cellulose nanocrystallites as an efficient support for nano-particles of palladium: application for catalytic hydrogenation and Heck coupling under mild conditions. Green Chem 13:288–291CrossRef

Clark JH, Macquarrie DJ (2002) Green chemistry and technology. Blackwell, AbingdonCrossRef

Dounay AB, Overman LE (2003) The asymmetric intramolecular Heck reaction in natural product total synthesis. Chem Rev 103:2945–2963CrossRef

Du Q, Li Y (2011) Air-stable, recyclable, and time-efficient diphenylphosphinite cellulose-supported palladium nano-particles as a catalyst for Suzuki–Miyaura reactions. Beilstein J Org Chem 7:378–385CrossRef

Ermakov YI, Aezamaskova LN (1986) Supported metal complexes as hydrogenation catalysts. Stud Surf Sci Catal 27:459–464CrossRef

Farina V (2004) High-turnover palladium catalysts in cross-coupling and Heck chemistry: a critical overview. Adv Synth Catal 346:1553–1582CrossRef

Guibal E (2005) Heterogeneous catalysis on chitosan-based materials: a review. Prog Polym Sci 30:71–109CrossRef

Heck RF (1982) Palladium-catalyzed vinylation of organic halides. Org React 27:345–390

Klemm D, Heublein B, Fink HP, Bohn A (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed 44:3358–3393CrossRef

Reddy KR, Kumar NS, Reddy PS, Sreedhar B, Kantam ML (2006) Cellulose supported palladium(0) catalyst for Heck and Sonogashira coupling reactions. J Mol Catal A: Chem 252:12–16CrossRef

Schwarz J, Bohm VPW, Gardiner MG, Grosche M, Herrmann WA, Hieringer W, Raudaschl-Sieber G (2000) Polymer-supported carbene complexes of palladium: well-defined, air-stable, recyclable catalysts for the Heck reaction. Chem Eur J 6:1773–1780CrossRef

Shaabani A, Maleki A (2007) Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot three-component synthesis of α-amino nitriles. Appl Catal A 331:149–151CrossRef

Shaabani A, Maleki A, Rad JM, Soleimani E (2007) Cellulose sulfuric acid catalyzed one-pot three-component synthesis of imidazoazines. Chem Pharm Bull 55:957–958CrossRef

Shaabani A, Rahmati A, Badri Z (2008) Sulfonated cellulose and starch: new biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines. Catal Commun 9:13–16CrossRef

Shaabani A, Seyyedhamzeh M, Maleki A, Rezazadeh F (2009) Cellulose sulfuric acid: an efficient biopolymer-based catalyst for the synthesis of oxazolines, imidazolines and thiazolines under solvent-free conditions. Appl Catal A 358:146–149CrossRef

Sonogashira KJ (2002) Development of Pd/Cu catalyzed cross-coupling of terminal acetylenes with sp²-carbon halides. Organomet Chem 653:46–49CrossRef

Varma RS, Naicker KP, Liesen PJ (1999) Palladium chloride/tetraphenylphosphonium bromide intercalated clay: new catalyst for cross-coupling of aryl halides with arylboronic acids. Tetrahedron Lett 40:2075–2079CrossRef

Wagner M, Kohler K, Djakovitch L, Weinkauf S, Hagen V, Muhler M (2000) Heck reactions catalyzed by oxide-supported palladium-structure-activity relationships. Top Catal 13:319–326CrossRef

Wali A, Pillai SM, Kaushik VK, Satish S (1996) Arylation of acrylonitrile with iodobenzene over Pd/MgO catalyst. Appl Catal A Gen 135:83–93CrossRef

Xu Y, Zhang L, Cui Y (2008) Catalytic performance of cellulose supported palladium complex for Heck reaction in water. J Appl Polym Sci 110:2996–3000CrossRef

Yang YF, Zhuang M, Zeng CX, Huang CB, Luo MF (2006) Ethylenediamine-functionalized resin-supported Pd(0) complex: an effective and recyclable catalyst for Heck vinylation. Chin J Chem 24:1309–1314CrossRef

Zhao F, Bhanage BM, Shirai M, Arai M (2000) Heck reactions of iodobenzene and methyl acrylate with conventional supported palladium catalysts in the presence of organic and/or inorganic bases without ligands. Chem Eur J 6:843–848CrossRef

Zhou JM, Zhou RX, Mo LY, Zhao SF, Zheng XM (2001) MCM-41 Supported aminopropylsiloxane palladium acetate complex: a highly active and stereoselective catalyst for Heck reaction. Chin J Chem 19:987–990CrossRef

Titel: Palladium nano-particles supported on ethylenediamine-functionalized cellulose as a novel and efficient catalyst for the Heck and Sonogashira couplings in water
verfasst von: Sajjad Keshipour
Salman Shojaei
Ahmad Shaabani
Publikationsdatum: 01.04.2013
Verlag: Springer Netherlands
Erschienen in: Cellulose / Ausgabe 2/2013
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-012-9852-8

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