Preparation of a PEG-supported ligand as highly stable palladium catalyst and its efficient recyclability in the heck reaction

Synthetic Communications

Volumn 37, Issue 2, 2007, Pages 191-197

  Zhang, Hua Xing ^a   Luo, Cheng Cai ^a   Jin, Ting ^a   Luo, Xi Ping ^b  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG A F UNIVERSITY   (China)

Author keywords

Heck reaction; Palladium; PEG; Supported ligands

Indexed keywords

LIGAND; MACROGOL; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; DEGRADATION KINETICS; HECK REACTION; PHYSICAL CHEMISTRY;

EID: 33846992663     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910601031595     Document Type: Article

References (14)

1. Heck, R. F.; Nolley, J. P. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem. 1972, 37, 2320.
2. Beletskaya, I. P.; Cheprakov, A. V. The Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev. 2000, 100, 3009.
3. Dounary, A. B.; Overman, L. E. The asymmetric intramolecular Heck reaction in natural product total synthesis. Chem. Rev. 2003, 103, 2945.
4. Braase, S.; De Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, D. J., (Eds.); Wiley-VCH: Weinheim, 1998.
5. Garb, D. In Ullmann's Encydopaedia of Industrial Chemistry; Wiley-VCH: Weinheim, 1999; Vol. A7.
6. Zhao, F.; Bhanage, B. M.; Shirai, M.; Arai, M. 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. 2000, 6, 843.
7. Augustine, R. L.; O'Leazy, S. T. Heterogeneous catalysis in organic chemistry, part 8: The use of supported palladium catalysts for the Heck arylation. J. Mol. Catal. 1992, 72, 229.
8. Mehnert, C. P.; Ying, J. Y. Palladium-grafted mesoporous MCM-41 material as heterogeneous catalyst for Heck reactions. Chem. Commun. 1997, 2215.
9. Mehnert, C. P.; Weaver, D. W.; Ying, J. Y. Heterogeneous Heck catalysis with palladium-grafted molecular sieves. J. Am. Chem. Soc. 1998, 120, 12289.
10. Bergbreiter, D. E.; Osburn, P. L.; Liu, Y. S. Tridentate SCS palladium(II) Complexes: New, highly stable, recyclable catalysts for the Heck reaction. J. Am. Chem. Soc. 1999, 121, 9531.
11. Heldebrant, D. J.; Jessop, P. G. Liquid poly(ethylene glycol) and supercritical carbon dioxide: A benign biphasic solvent system for use and recycling of homogeneous catalysts. J. Am. Chem. Soc. 2003, 125, 5600.
12. Rogers, R. D.; Bond, A. H.; Roden, D. M. Structural chemistry of poly(ethylene glycol) complexes of lead(II) nitrate and lead(II) bromide. Inorg. Chem. 1996, 35, 6864.
13. Bernson, A.; Lindgren, J.; Huang, W.; Frech, R. Coordination and conformation in PEO, PEGM, and PEG systems containing lithium or lanthanum triflate. Polymer 1995, 36, 4471.
14. Horvath, G.; Rusa, C.; Kontos, Z.; Gerencser, J.; Huszthy, P. A new efficient method for the preparation of 2,6-pyridinedimethyl ditosylates from dimethyl 2,6-pyridinedicarboxylates. Synth. Commun. 1999, 29 (21), 3719.