Recyclable nanostructured catalytic systems in modern environmentally friendly organic synthesis

Molecules

Volumn 15, Issue 7, 2010, Pages 4792-4814

  Beletskaya, Irina ^a,b   Tyurin, Vladimir ^a  

^a FRUMKIN INSTITUTE OF PHYSICAL CHEMISTRY AND ELECTROCHEMISTRY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Anocatalysts; Catalysis; Catalyst recycling; Green Chemistry; Nanoparticles; Polymer supported catalysts

Indexed keywords

NANOMATERIAL;

CATALYSIS; GREEN CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY; RECYCLING; REVIEW;

CATALYSIS; CHEMISTRY, ORGANIC; GREEN CHEMISTRY TECHNOLOGY; NANOSTRUCTURES; RECYCLING;

EID: 77954978352     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15074792     Document Type: Review

References (45)

1. Widegren, J.A.; Finke, R.G. A review of the problem of distinguishing true homogeneous catalysis from soluble or other metal-particle heterogeneous catalysis under reducing conditions. J. Mol. Catal. A: Chem. 2003, 198, 317-341.
2. Reetz, M.T.; de Vries, J.G. Ligand-free Heck reactions using low Pd-loading. Chem. Commun. 2004. P. 1559-1563.
3. Beletskaya, I.P; Cheprakov, A.V. Palladacycles in catalysis - a critical survey. J. Organometal. Chem. 2004, 689, 4055-4082.
4. Lewis, L.N. Chemical catalysis by colloids and clusters. Chem. Rev. 1993, 93, 2693-2730.
5. Trzeciak, A.M.; Zióllkowski, J.J. Monomolecular, nanosized and heterogenized palladium catalysts for the Heck reaction. Coord. Chem. Rev. 2007, 251, 1281-1293.
6. Zhao, D.; Fei, Z.; Geldbach, T.J.; Scopelliti, R.; Dyson, P.J. Nitrile Functionalized Pyridinium Ionic Liquids: Synthesis, Characterization, and Their Application in Carbon-Carbon Coupling Reactions. J. Am. Chem. Soc. 2004, 126, 15876-15882.
7. Ananikov, V.P.; Beletskaya, I.P. Using Nanosized, Homogeneous, and Heterogeneous Catalytic Systems in Organic Synthesis: Changing the Structure of Active Center in Chemical Reactions in Solution. Nanotechnol. Russ. 2010, 5, 1-17.
8. Anastas, P.T.; Warner, J. Green Chemistry: Theory and Practice; Oxford University Press: New York, NY, USA, 2000.
9. Bumagin, N.A.; Bykov, V.V.; Beletskaya, I.P. Synthesis of diaryls from phenylboric acid and aryl iodides in an aqueous medium. Russ. Chem. Bull. 1989, 38, 2206.
10. Beletskaya I.P. Palladium-catalyzed Organic Reactions in Aqueous Media. In New Aspects of Organic Chemistry II. Organic Synthesis for Material and Life Sciences; Kodausha: Tokyo, Japan, 1992; pp. 31-41.
11. Beletskaya, I.P.; Cheprakov, A.V. Aqueous transition metal catalysis. In Organic Synthesis in Water; Grieco, P.A., Ed.; Blackie Academic & Professional: London, UK, 1998; pp. 141-222.
12. Beletskaya, I.P.; Cheprakov, A.V. Aqueous Palladium Catalysis. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons, Inc.: New York, NY, USA, 2002; Volume 2, pp. 2955-3006.
13. Cheprakov, A.V.; Ponomareva, N.V.; Beletskaya, I.P. Palladium catalyzed carbonylation of iodoarenes in aqueous solubilized systems. J. Organometal. Chem. 1995, 486, 297-300.
14. Bergbreiter, D.E.; Tian, J.; Hongfa, C. Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis. Chem. Rev. 2009, 109, 530-582
15. Hamley, I.W. Nanostructure fabrication using block copolymers. Nanotechnology 2003, 14, R39-R54.
16. Bronstein, L.M.; Sidorov, S.N.; Valetsky, P.M. Nanostructured polymeric systems as nanoreactors for nanoparticle formation. Russ. Chem. Rev. 2004, 73, 501-515.
17. Klingelhofer, S.; Heitz, W.; Greiner, A.; Oestreich, S.; Forster, S.; Antonietti, M. Preparation of Palladium Colloids in Block Copolymer Micelles and Their Use for the Catalysis of the Heck Reaction. J. Am. Chem. Soc. 1997, 119, 10116-10120.
18. Li, Y.; El-Sayed, M.A. The Effect of Stabilizers on the Catalytic Activity and Stability of Pd Colloidal Nanoparticles in the Suzuki Reactions in Aqueous Solution. J. Phys. Chem. B. 2001, 105, 8938-8943.
19. Beletskaya, I.P.; Kashin, A.N.; Litvinov, A.E.; Tyurin, V.S.; Valetsky, P.M.; van Koten G. Palladium Colloid Stabilized by Block Copolymer Micelles as an Efficient Catalyst for Reactions of C-C and C-Heteroatom Bond Formation. Organometallics 2006, 25, 154-158.
20. Beletskaya, I.P.; Kashin, A.N.; Khotina, I.A.; Khokhlov, A.R. Efficient and Recyclable Catalyst of PdNPs Stabilized by Polymer Micelles Soluble in Water for Suzuki-Miyaura Reaction, Ostwald Ripening Process with PdNPs. Synlett 2008, 1547-1552.
21. Calò, V.; Giannoccaro, P.; Nacci, A.; Monopoli, A. Pd-benzothiazole carbene catalysed carbonylation of aryl halides in ionic liquids. J. Organometal. Chem. 2002, 645, 152-157.
22. Brennführer, A.; Neumann, H.; Beller, M. Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds. Angew. Chem. Int. Ed. 2009, 48, 4114-4133.
23. Beletskaya, I.P.; Ganina, O.G. Hydroxy- and alkoxycarbonylation of aryl iodides catalyzed by polymer-supported palladium. React. Kinet. Mech. Catal. 2010, 99, 1-4.
24. Beletskaya, I.P.; Khokhlov, A.R.; Tarasenko, E.A.; Tyurin, V.S. Palladium supported on poly(N-vinylimidazole) or poly(N-vinylimidazole-co-N- vinylcaprolactam) as a new recyclable catalyst for the Mizoroki-Heck reaction. J. Organometal. Chem. 2007, 692, 4402-4406.
25. Beletskaya, I.P.; Selivanova, A.V.; Tyurin, V.S.; Matveev, V.V.; Khokhlov, A.R. Palladium Nanoparticles Stabilized by a Copolymer of N-Vinylimidazole with N-Vinylcaprolactam as Efficient Recyclable Catalyst of Aromatic Cyanation. Russ. J. Org. Chem. 2010, 46, 157-161.
26. Schareina, T.; Zapf, A.; Beller, M. Potassium hexacyanoferrate(II)-a new cyanating agent for the palladium-catalyzed cyanation of aryl halides. Chem. Commun. 2004, 1388-1389.
27. Zhu, Y.-Z.; Cai, C. Pd/C: A Recyclable Catalyst for Cyanation of Aryl Bromides. Eur. J. Org. Chem. 2007, 2401-2404.
28. Bender, M.L.; Bergeron, R.J.; Komiyama, M. The Bioorganic Chemistry of Enzymatic Catalysis; John Wiley & Sons, Inc.: New York, NY, USA, 1984.
29. Lozinsky, V.I.; Simenel, I.A.; Kulakova, V.K.; Kurskaya, E.A.; Babushkina, T.A.; Klimova, T.P., Burova, T.V.; Dubovik, A.S.; Grinberg, V.Y.; Galaev, I.Y.; Mattiasson, B.; Khokhlov, A.R. Synthesis and Studies of N-Vinylcaprolactam/N-Vinylimidazole Copolymers that Exhibit the "Proteinlike" Behavior in Aqueous Media. Macromolecules 2003, 36, 7308-7323.
30. Okhapkin, I.M.; Bronstein, L.M.; Makhaeva, E.E.; Matveeva, V.G.; Sulman, E.M.; Sulman, M.G.; Khokhlov, A.R. Thermosensitive Imidazole-Containing Polymers as Catalysts in Hydrolytic Decomposition of p-Nitrophenyl Acetate. Macromolecules 2004, 37, 7879-7883.
31. Beletskaya, I.P.; Tarasenko, E.A.; Khokhlov, A.R.; Tyurin, V.S. Poly(N-vinylimidazole) as Efficient and Recyclable Catalyst for the Addition of Thiols to Michael Acceptors in Aqueous Medium. Russ. J. Org. Chem. 2007, 43, 1733-1736.
32. Beletskaya, I.P.; Tarasenko, E.A.; Khokhlov, A.R.; Tyurin, V.S. Poly(N-vinylimidazole) as Efficient and Recyclable Catalyst of the Aza-Michael Reaction in Water. Russ. J. Org. Chem. 2010, 46, 461-467.
33. Beletskaya, I.P.; Tarasenko, E.A.; Khokhlov, A.R.; Tyurin, V.S. CH-Acids in the Michael Reaction Catalyzed by the Polymer Base. Russ. J. Org. Chem. 2010, 46, in press.
34. Toshima, N.; Yonezawa, T. Bimetallic nanoparticles - novel materials for chemical and physical applications. New J. Chem. 1998, 22, 1179-1201.
35. Nikolaev, S.A.; Smirnov, V.V.; Beletskaya, I.P.; Vasilkov, A.Y.; Naumkin, A.V.; Tyurina, L.A. Synergism of the Catalytic Action of Au-Ni Nano composites in the Course of Allyl Isomerization of Allylbenzene. Ross. Nanotekhnol. 2007, 2, 58.
36. Lin, S.T.; Franklin, M.T.; Klabunde, K.J. Nonaqueous colloidal gold. Clustering of metal atoms in organic media. Langmuir 1986, 2, 259-260.
37. Ananikov, V.P.; Kabeshov, M.A.; Beletskaya, I.P. The first example or polymer-supported palladium catalyst for stereoselective S-S bond addition to terminal alkynes. Synlett 2005, 1015-1017.
38. Ananikov, V.P.; Beletskaya, I.P. Solvent-free palladium-catalyzed addition of diaryl dichalcogenides to alkynes. Russ. Chem. Bull. 2004, 53, 561-565.
39. Ananikov, V.P.; Gayduk, K.A.; Beletskaya, I.P.; Khrustalev, V.N.; Antipin, M.Y. Remarkable ligand effect in Ni- and Pd-catalyzed bisthiolation and bisselenation of terminal alkynes: Solving the problem of stereoselective dialkyldichalcogenide addition to the C=C bond. Chem. Eur. J. 2008, 14, 2420-2434.
40. Ananikov, V.P.; Orlov, N.V.; Beletskaya, I.P. Efficient and Convenient Synthesis of β-Vinyl Sulfides in Nickel-Catalyzed Regioselective Addition of Thiols to Terminal Alkynes under Solvent-Free Conditions. Organometallics 2006, 25, 1970-1977.
41. Ananikov, V.P.; Orlov, N.V.; Beletskaya, I.P. Highly Efficient Nickel-Based Heterogeneous Catalytic System with Nanosized Structural Organization for Selective Se-H Bond Addition to Terminal and Internal Alkynes. Organometallics 2007, 26, 740-750.
42. Malyshev, D.A.; Scott, N.M.; Marion, N.; Stevens, E.D.; Ananikov, V.P.; Beletskaya, I.P.; Nolan, S.P. Homogeneous Nickel Catalysts for the Selective Transfer of a Single Arylthio Group in the Catalytic Hydrothiolation of Alkynes. Organometallics 2006, 25, 4462-4470.
43. Beletskaya, I.P.; Ananikov, V.P. Unusual Influence of the Structures of Transition Metal Complexes on Catalytic C-S and C-Se Bond Formation under Homogeneous and Heterogeneous Conditions. Eur. J. Org. Chem. 2007, 21, 3431-3444.
44. Malyshev, D.A.; Scott, N.M.; Marion, N.; Stevens, E.D.; Ananikov, V.P.; Beletskaya, I.P.; Nolan, S.P. Homogeneous Nickel Catalysts for the Selective Transfer of a Single Arylthio Group in the Catalytic Hydrothiolation of Alkynes. Organometallics 2006, 25, 4462-4470.
45. Ananikov, V.P.; Orlov, N.V.; Beletskaya, I.P.; Khrustalev, V.N.; Antipin, M.Y.; Timofeeva, T.V. New Approach for Size- and Shape-Controlled Preparation of Pd Nanoparticles with Organic Ligands. Synthesis and Application in Catalysis. J. Am. Chem. Soc. 2007, 129, 7252-7253.