Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations

Angewandte Chemie - International Edition

Volumn 43, Issue 29, 2004, Pages 3754-3760

  Ajamian, Alain ^a   Gleason, James L ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Catalysis; Domino reactions; Metathesis; Pauson Khand reaction; Transition metals

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; SYNTHESIS (CHEMICAL);

BOND FORMATION; REACTION SEQUENCES; SINGLE-POT CATALYSIS;

METALLIC COMPOUNDS;

BENZENE DERIVATIVE; CARBON; HYDROGEN; METAL;

CATALYSIS; CATALYST; CHEMICAL BOND; SHORT SURVEY;

EID: 4544376543     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200301727     Document Type: Short Survey

References (40)

1. R. B. Woodward, M. P. Cav, W. D. Ollis, A. Hunger, H. U. Daeniker, K. Schenker, J. Am. Chem. Soc. 1954, 76, 4749.
2. For reviews of metal-catalyzed and metal-mediated domino and sequenced reactions, see: a) M. Malacria, Chem. Rev. 1996, 96, 289;
3. b) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307;
4. c) A. de Meijere, S. Bräse, J. Organomet. Chem. 1999, 576, 88;
5. d) R. Grigg, V. Sridharan, J. Organomet. Chem. 1999, 576, 65;
6. e) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959;
7. f) A. de Meijere, M. Schelper, Actual. Chim. 2003, 51.
8. These definitions are analogous to "consecutive" and "domino" reactions as defined by Tietze; see: L. F. Tietze, U. Beifuss, Angew. Chem. 1993,105,137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
9. These definitions are analogous to "consecutive" and "domino" reactions as defined by Tietze; see: L. F. Tietze, U. Beifuss, Angew. Chem. 1993,105,137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
10. These definitions are analogous to "consecutive" and "domino" reactions as defined by Tietze; see: L. F. Tietze, U. Beifuss, Angew. Chem. 1993,105,137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
11. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18.
12. S. J. McLain, S. D. Arthur, E. Hauptman, J. Feldman, W. A. Nugent, L. K. Johnson, S. Mecking, M. Brookhart, Polym. Mater. Sci. Eng. 1997, 76, 246.
13. E. L. Dias, R. H. Grubbs, Organometallics 1998, 17, 2767.
14. M. D. Watson, K. B. Wagener, Macromolecules 2000, 33, 3196.
15. S. D. Drouin, F. Zamanian, D. E. Fogg, Organometallics 2001, 20, 5495.
16. J. Louie, C. W. Bielawski, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 11312.
17. A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320; Angew. Chem. Int. Ed. 2003, 42, 308.
18. A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320; Angew. Chem. Int. Ed. 2003, 42, 308.
19. P. A. Evans, J. E. Robinson, J. Am. Chem. Soc. 2001, 123, 4609.
20. E. Teoh, E. M. Campi, W. R. Jackson, A. J. Robinson, Chem. Commun. 2002, 978.
21. a) A. N. Thadani, V. H. Rawal, Org. Lett. 2002, 4, 4317;
22. b) A. N. Thadani, V. H. Rawal, Org. Lett. 2002, 4, 4321.
23. J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2002, 114, 3788; Angew. Chem. Int. Ed. 2002, 41, 3636.
24. J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2002, 114, 3788; Angew. Chem. Int. Ed. 2002, 41, 3636.
25. H. Du, K. Ding, Org. Lett. 2003, 5, 1091.
26. F. Simal, A. Demonceau, A. F. Noels, Angew. Chem. 1999, 111, 559; Angew. Chem. Int. Ed. 1999, 38, 538.
27. F. Simal, A. Demonceau, A. F. Noels, Angew. Chem. 1999, 111, 559; Angew. Chem. Int. Ed. 1999, 38, 538.
28. C. W. Bielawski, J. Louie, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 12872.
29. A. E. Sutton, B. A. Seigal, D. F. Finnegan, M. L. Snapper, J. Am. Chem. Soc. 2002, 124, 13390.
30. B. Schmidt, M. Pohler, Org. Biomol. Chem. 2003, 1, 2512;
31. b) B. Schmidt, Eur. J. Org. Chem. 2003, 816.
32. a) S. U. Son, D. S. Choi, Y. K. Chung, S.-G. Lee, Org. Lett. 2000, 2, 2097;
33. b) S. U. Son, K. H. Park, Y. K. Chung, Org. Lett. 2002, 4, 3983.
34. T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Am. Chem. Soc. 2002, 124, 3806.
35. T. Shibata, N. Toshida, K. Takagi, Org. Lett. 2002, 4, 1619;
36. b) T. Shibata, N. Toshida, K. Takagi, J. Org. Chem. 2002, 67, 7446; tolbinap = (-)-2,2′-bis(di-p-tolylphosphanyl)-1,1′-binaphthyl.
37. K. Fuji, T. Morimoto, K. Tsutsumi, K. Kakiuchi, Angew. Chem. 2003, 115, 2511; Angew. Chem. Int. Ed. 2003, 42, 2409; SDS = sodium dodecylsulfate, TPPTS = triphenylphosphane-(3,3′,3″)-trisulfonic acid trisodium salt.
38. K. Fuji, T. Morimoto, K. Tsutsumi, K. Kakiuchi, Angew. Chem. 2003, 115, 2511; Angew. Chem. Int. Ed. 2003, 42, 2409; SDS = sodium dodecylsulfate, TPPTS = triphenylphosphane-(3,3′,3″)-trisulfonic acid trisodium salt.
39. I. Sakurada, S. Yamasaki, R. Göttlich, T. Iida, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 1245;
40. b) S. Yamasaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 1256.