A convergence of homogeneous and heterogeneous catalysis: Immobilized organometallic catalysts

Model Systems in Catalysis: Single Crystals to Supported Enzyme Mimics

Volumn , Issue , 2010, Pages 441-455

  Shiels, Rebecca A ^a   Jones, Christopher W ^a  

^a Georgia Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84890169484     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-0-387-98049-2_20     Document Type: Chapter

References (49)

1. Severn JR, Chadwick JC, Duchateau R, Friederichs N (2005) "Bound but Not Gagged" - immobilizing single-site a-olefin polymerization catalysts. Chem Rev 105:4073.
2. McMorn P, Hutchings GJ (2004) Heterogeneous enantioselective catalysts: Strategies for the immobilisation of homogeneous catalysts. Chem Soc Rev 33:108.
3. Wight AP, Davis ME (2002) Design and preparation of organic-inorganic hybrid catalysts. Chem Rev 102:3589.
4. Ying JY, Mehnert CP, Wong MS (1999) Synthesis and applications of supramolecular-templated mesoporous materials. Angew Chem Int Ed 38:56.
5. Burkett SL, Sims SD, Mann S (1996) Synthesis of hybrid inorganic-organic mesoporous silica by co-condensation of siloxane and organosiloxane precursors. Chem Commun 1367.
6. Sayari A, Hamoudi S (2001) Periodic mesoporous silica-based organic-inorganic nanocomposite materials. Chem Mater 13:3151.
7. Fryxell GE (2006) The synthesis of functional mesoporous materials. Inorg Chem Commun 9:1141.
8. Wulff G, Heide B, Helfmeier G (1986) Molecular recognition through the exact placement of functional groups on rigid matrices via a template approach. J Am Chem Soc 108:1089.
9. Katz A, Davis ME (2000) Molecular imprinting of bulk, microporous silica. Nature 403:286.
10. Bass JD, Katz A (2003) Thermolytic synthesis of imprinted amines in bulk silica. Chem Mater 15:2757.
11. Bass JD, Anderson SL, Katz A (2003) The effect of outer-sphere acidity on chemical reactivity in a synthetic heterogeneous base catalyst. Angew Chem Int Ed 42:5219.
12. McKittrick MW, Jones CW (2003) Toward single-site functional materials - preparation of amine-functionalized surfaces exhibiting site-isolated behavior. Chem Mater 15:1132.
13. Hicks JC, Jones CW (2006) Controlling the density of amine sites on silica surfaces using benzyl spacers. Langmuir 22:2676.
14. McKittrick MW, Jones CW (2004) Toward single-site, immobilized molecular catalysts: Site-isolated Ti ethylene polymerization catalysts supported on porous silica. J Am Chem Soc 126:3052.
15. Yu K, McKittrick MW, Jones CW (2004) Role of amine structure and site isolation on the performance of aminosilica-immobilized Zirconium CGC-inspired ethylene polymerization catalysts. Organometallics 23:4089.
16. McKittrick MW, Jones CW (2004) Effect of site isolation on the preparation and performance of silica-immobilized Ti CGC-inspired ethylene polymerization catalysts. J Catal 227:186.
17. McKittrick MW, Yu K, Jones CW (2005) Effect of metallation protocol on the preparation and performance of silica-immobilized Ti CGC-inspired ethylene polymerization catalysts. J Mol Catal A 237:26.
18. McKittrick MW, Jones CW (2005) Modulating the reactivity of an organometallic catalyst via immobilization on a spatially patterned silica surface. Chem Mater 17:4758.
19. Hicks C, Dabestani R, Buchanan AC III, Jones CW (2008) Assessing Site-Isolation of Amine Groups on Aminopropyl-Functionalized SBA-15 Materials via Spectroscopic and Reactivity Probes. Inorg. Chim. Acta 361:3024-3032.
20. Hicks JC, Dabestani R, Buchanan AC III, Jones CW (2006) Spacing and site isolation of amine groups in 3-aminopropyl-grafted silica materials: The role of protecting groups. Chem Mater 18:5022.
21. Chen EY-X, Marks TJ (2000) Cocatalysts for metal-catalyzed olefin polymerization: Activators, activation processes, and structure-activity relationships. Chem Rev 100:1391.
22. Hicks JC, Mullis BA, Jones CW (2007) Sulfonic acid functionalized SBA-15 silica as a methylaluminoxane- free cocatalyst/support for ethylene polymerization. J Am Chem Soc 129:8426.
23. Yu K, Jones CW (2003) Silica-immobilized Zinc B-diiminate catalysts for the copolymerization of epoxides and carbon dioxide. Organometallics 22:2571.
24. Wang J-S, Matyjaszewski K (1995) Controlled/"Living" radical polymerization. Atom transfer radical polymerization in the presence of transition-metal complexes. J Am Chem Soc 117:5614.
25. Wang J-S, Matyjaszewski K (1995) "Living"/controlled radical polymerization. Transitionmetal- catalyzed atom transfer radical polymerization in the presence of a conventional radical initiator. Macromolecules 28:7572.
26. Wang J-S, Matyjaszewski K (1995) Controlled/"Living" radical polymerization. Halogen atom transfer radical polymerization promoted by a Cu(I)/Cu(II) redox process. Macromolecules 28:7901.
27. Kato M, Kamigaito M, Sawamoto M, Higashimura T (1995) Polymerization of methyl methacrylate with the carbon tetrachloride/ dichlorotris(triphenylphosphine)ruthenium(II)/Methylaluminum bis(2, 6-di-tert-butylphenoxide) initiating system: possibility of living radical polymerization. Macromolecules 28:1721.
28. Matyjaszewski K, Xia J (2001) Atom transfer radical polymerization. Chem Rev 101:2921.
29. Hong SC, Paik H-J, Matyjaszewski K (2001) An immobilized/soluble hybrid catalyst system for atom transfer radical polymerization. Macromolecules 34:5099.
30. Haddleton DM, Duncalf DJ, Kukulj D, Radigue AP (1999) 3-Aminopropyl silica supported living radical polymerization of methyl methacrylate: dichlorotris(triphenylphosphine) ruthenium(ii) mediated atom transfer polymerization. Macromolecules 32:4769.
31. Honigfort ME, Brittain WJ (2003) Use of JandaJel resins for copper removal in atom transfer radical polymerization. Macromolecules 36:3111.
32. Hong SC, Matyjaszewski K (2002) Fundamentals of supported catalysts for Atom Transfer Radical Polymerization (ATRP) and application of an immobilized/soluble hybrid catalyst system to ATRP. Macromolecules 35:7592.
33. Nguyen JV, Jones CW (2004) Effect of the synthetic method and support porosity on the structure and performance of silica-supported CuBr/Pyridylmethanimine atom transfer radical polymerization catalysts. I. Catalyst preparation and characterization. J Polym Sci. Part A 42:1367.
34. Nguyen JV, Jones CW (2004) Effect of the synthetic method and support porosity on the structure and performance of silica-supported CuBr/pyridylmethanimine atom transfer radical polymerization catalysts. II. Polymerization of methyl methacrylate. J Polym Sci. Part A 42:1384.
35. Nguyen JV, Jones CW (2004) Design, behavior, and recycling of silica-supported CuBr- Bipyridine ATRP catalysts. Macromolecules 37:1190.
36. Nguyen JV, Jones CW (2005) Recyclable polymerization catalysts: methyl methacrylate polymerization with silica-supported CuBr-bipyridine atom transfer radical polymerization catalysts. J Catal 232:276.
37. Blaser H-U, Indolese A, Naud F, Nettekoven U, Schnyder A (2004) Industrial R&D on catalytic C-C and C-N coupling reactions: A personal account on goals, approaches and results. Adv Synth Catal 346:1583.
38. Weck M, Jones CW (2007) Mizoroki-Heck coupling using immobilized molecular precatalysts: leaching active species from Pd Pincers, entrapped Pd Salts, and Pd NHC complexes. Inorg Chem 46:1865.
39. Gruber AS, Zim D, Ebeling G, Monteiro AL, Dupont J (2000) Sulfur-containing palladacycles as catalyst precursors for the Heck reaction. Org Lett 2:1287.
40. Bergbreiter DE, Osburn PL, Liu Y-S (1999) Tridentate SCS Palladium(II) complexes: new, highly stable, recyclable catalysts for the Heck reaction. J Am Chem Soc 121:9531.
41. Bergbreiter DE, Osburn PL, Wilson A, Sink EM (2000) Palladium-catalyzed c-c coupling under thermomorphic conditions. J Am Chem Soc 122:9058.
42. Beller M, Riermeier TH (1998) Palladium-catalyzed reactions for fine chemical synthesis Part 4 Phosphapalladacycle-catalyzed Heck reactions for efficient synthesis of trisubstituted olefins Evidence for palladium(0) intermediates. Eur J Inorg Chem 1998:29.
43. Consorti CS, Flores FR, Dupont J (2005) Kinetics and mechanistic aspects of the Heck reaction promoted by a CN-Palladacycle. J Am Chem Soc 127:12054.
44. Yu K, Sommer W, Weck M, Jones CW (2004) Silica and polymer-tethered Pd-SCS-pincer complexes: Evidence for precatalyst decomposition to form soluble catalytic species in Mizoroki-Heck chemistry. J Catal 226:101.
45. Yu K, Sommer W, Richardson JM, Weck M, Jones CW (2005) Evidence that SCS Pincer Pd(II) Complexes are only Precatalysts in Heck Catalysis and the Implications for Catalyst Recovery and Reuse. Adv Synth Catal 347:161.
46. Sommer W, Yu K, Sears JS, Ji Y, Zheng X, Davis RJ, Sherrill CD, Jones CW, Weck M (2005) Investigations into the stability of tethered palladium(II) pincer complexes during Heck catalysis. Organometallics 24:4351.
47. Richardson JM, Jones CW (2006) Poly(4-vinylpyridine) and quadrapure TU as selective poisons for soluble catalytic species in palladium-catalyzed coupling reactions - Application to leaching from polymer-entrapped palladium. Adv Synth Catal 348:1207.
48. Phan NTS, Van Der Sluys M, Jones CW (2006) On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings - homogeneous or heterogeneous catalysis: A critical review. Adv Synth Catal 348:609.
49. Phan NTS, Gill CS, Nguyen JV, Zhang ZJ, Jones CW (2006) Expanding the utility of one-pot multistep reaction networks through compartmentation and recovery of the catalyst. Angew Chem Int Ed 45:2209.