Ammonium formate/palladium on carbon: A versatile system for catalytic hydrogen transfer reductions of carbon-carbon double bonds

Synthesis

Volumn , Issue 13, 2003, Pages 2023-2026

  Paryzek, Zdzisław ^a   Koenig, Hanna ^a   Tabaczka, Bartłomiej ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Ammonium formate; Catalytic transfer hydrogenations; Olefins; Reduction; , unsaturated ketones

Indexed keywords

CATALYSTS; CHEMICAL BONDS; KETONES; METHANOL; OLEFINS;

HYDROGEN TRANSFER AGENTS;

SYNTHESIS (CHEMICAL);

ALKANE DERIVATIVE; ALKENE; AMMONIUM FORMATE; CARBON; HYDROGEN; KETONE DERIVATIVE; METHANOL; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REDUCTION;

EID: 0141841628     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41024     Document Type: Article

References (50)

1. Brieger, G.; Nestrick, T. J. Chem. Rev. 1974, 74, 567.
2. Johnstone, R. A. W.; Wilby, A. H.; Entwistle, J. D. Chem. Rev. 1985, 85, 129; and references cited therein.
3. Anderson, J. R. Structure of Metallic Catalysts; Academic Press: New York, 1975.
4. Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91.
5. Gartiser, T.; Selve, C.; Delpuech, J. J. Tetrahedron Lett. 1983, 24, 1609.
6. Entwistle, I. D.; Jackson, A. E.; Johnstone, R. A. W.; Telford, R. P. J. Chem. Soc., Perkin Trans. 1 1977, 443.
7. (a) Ram, S.; Ehrenkaufer, R. E. Tetrahedron Lett. 1984, 25, 3415.
8. (b) Ram, S.; Ehrenkaufer, R. E. Synthesis 1986, 133. Kabalka, G. W.; Pace, R. D.; Wadgaonkar, P. P. Synth. Commun. 1990, 20, 2453.
9. (b) Ram, S.; Ehrenkaufer, R. E. Synthesis 1986, 133. Kabalka, G. W.; Pace, R. D.; Wadgaonkar, P. P. Synth. Commun. 1990, 20, 2453.
10. Brown, G. R.; Foubister, A. J. Synthesis 1982, 1036.
11. Ram S., Spicer L. D.; Tetrahedron Lett. 1988, 29: 3741.
12. Anwer, M. K.; Spatola, A. F. Tetrahedron Lett. 1985, 26, 1381.
13. Berdini, V.; Cesta, M. C.; Curti, R.; D'Anniballe, G.; Di Bello, N.; Nano, G.; Nicolini, L.; Topai, A.; Allegretti, M. Tetrahedron 2002, 58, 5669.
14. (a) Anwer, M. K.; Spatola, A. F. Synthesis 1980, 929.
15. (b) Anwer, M. K.; Spatola, A. F. J. Org. Chem. 1983, 48, 3503.
16. ElAmin, B.; Anantharamaiah, G. M.; Royer, G. P.; Means, G. E. J. Org. Chem. 1979, 44, 3442.
17. Bieg, T.; Szeja, W. Synthesis 1985, 76.
18. Zacharie, B.; Moreau, N.; Dockendorff, C. J. Org. Chem. 2001, 66, 5264.
19. Lee, S. H.; Park, Y. J.; Yoon, C. h. M. Tetrahedron Lett. 2000, 41, 887.
20. Tabaczka, B.; Paryzek, Z. Org. Prep. Proced. Int. 2001, 33, 400.
21. Hannon, S. J.; Kundu, N. G.; Hertzberg, R. P.; Shatt, R. S.; Heidelberger, C. Tetrahedron Lett. 1980, 21, 1105.
22. Nowak, P.; Błaszczyk, K.; Paryzek, Z. Org. Prep. Proced. Int. 1994, 26, 374.
23. Aranda, G.; Lallemand, J.-Y.; Azerad, R. Synth. Commun. 1994, 24, 2525.
24. Hammert, F. Bull. Soc. Chim. Fr. 1966, 976.
25. Loewenthal, H. J. E. Tetrahedron 1959, 269.
26. Pines, M. Steroids 1966, 31, 877.
27. Emmons, G. T.; Willson, W. K.; Schroepfer, G. J. Magn. Res. Chem. 1989, 27, 1012.
28. (a) Bentley, H. R.; Henry, J. A.; Irvine, D. S.; Spring, F. S. J. Chem. Soc. 1953, 3673.
29. (b) Nagai, M.; Ando, T.; Tanaka, N.; Tanaka, O.; Shibata, S. Chem. Pharm. Bull. 1972, 20, 1212.
30. (c) Mills, J. S. J. Chem. Soc. 1956, 2196.
31. (d) Marker, R. E.; Wittle, E. L.; Mixon, L. W. J. Am. Chem. Soc. 1937, 59, 1368.
32. Drefahl, G.; Ponsold, K.; Schick, H. Chem. Ber. 1965, 98, 604.
33. Dang, H. S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 2002, 1161.
34. Gschwendtner, W.; Schneider, H.-J. J. Org. Chem. 1980, 45, 3507.
35. Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469.
36. Jones, J. B.; Grayshan, R. Can. J. Chem. 1972, 60, 1407.
37. Li, X.; Singh, S.; Lobrie, F. Tetrahedron Lett. 1994, 35, 1157.
38. Westwell, A. D.; Williams, J. M. J. Tetrahedron 1997, 53, 13063.
39. Vepkhishvili, N. G.; Khananashvili, L. M.; Akhobadze, D. Sh.; Lomtatidze, Z. Sh.; Makharadze, N. G. Pharm. Chem. J. 1991, 25, 548; Chem. Abstr. 1991, 115, 183059.
40. Vepkhishvili, N. G.; Khananashvili, L. M.; Akhobadze, D. Sh.; Lomtatidze, Z. Sh.; Makharadze, N. G. Pharm. Chem. J. 1991, 25, 548; Chem. Abstr. 1991, 115, 183059.
41. Kaneniwa, N.; Ikekawa, A. Chem. Pharm. Bull. 1974, 22, 2990.
42. Jones, R. C. F.; Berthelot, D. J. C.; Iley, J. N. Tetrahedron 2001, 57, 6539.
43. Bergmann, E.; Heimhold, H. J. Chem. Soc. 1935, 1365.
44. Hopper, D. L.; Kaiser, R. Can. J. Chem. 1965, 43, 2363.
45. Stewart, T.; Reid, T.; Tucker, J. N.; Wilcox, E. J. J. Chem. Soc., Perkin Trans. 1 1974, 1359.
46. Nace, H. R.; Iacona, R. N. J. Org. Chem. 1964, 29, 3498.
47. Tachibana, K.; Sakaitami, M.; Koji, N. Tetrahedron 1965, 21, 102.
48. Kołek, T.; Małunowicz, J.; Mironowicz, A. Pol. J. Chem. 1979, 53, 453; Chem. Abstr. 1979, 91, 141089.
49. Kołek, T.; Małunowicz, J.; Mironowicz, A. Pol. J. Chem. 1979, 53, 453; Chem. Abstr. 1979, 91, 141089.
50. Nace, H. R.; Crosby, G. A. J. Org. Chem. 1979, 44, 3105.