Rhodium-catalyzed reductive cyclization of 1,6-diynes and 1,6-enynes mediated by hydrogen: Catalytic C-C bond formation via capture of hydrogenation intermediates

Journal of the American Chemical Society

Volumn 126, Issue 25, 2004, Pages 7875-7880

  Jang, Hye Young ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DATA ACQUISITION; PRESSURE EFFECTS; REDUCTION; THERMAL EFFECTS;

CYCLIZATION; DATA COLLECTION;

RHODIUM;

1 (2 METHYLCYCLOPENTYLIDENE)METHYLBENZENE; 1 BENZYLIDENE (2,3 DIHYDRO 2 METHYL 1H INDEN 3 YLOXY)(TERT BUTYL)DIMETHYLSILANE; 1,2 CYCLOPENTANE; 2,3 DIBENZYLIDENE 8,8 DIMETHYL 7,9 DIOXA SPIRO[4.5]DECANE 6,10 DIONE; 2,3 DIBENZYLIDENESPIRO[4.5]DECANE 6,10 DIONE; 3 BENZYLIDENE 4 ETHYLIDENECYCLOPENTANE 1,1 DICARBOXYLIC ACID DIMETHYL ESTER; 3 BENZYLIDENE 4 METHYL 1 TOSYLPYRROLIDINE; 3 BENZYLIDENE 4 TRIMETHYLSILANYLMETHYLENECYCLOPENTANE 1,1 DICARBOXYLIC ACID; 3 BENZYLIDENE TETRAHYDRO 4 METHYLFURAN; 3 ETHYLIDENE 4 METHYL 1 TOSYLPYRROLIDINE; 3,4 DIBENZYLIDENECYCLOPENTANE; 3,4 DIBENZYLIDENETETRAHYDROFURAN; 3,4 DIETHYLIDENE 1 (TOLUENE 4 SULFONYL)PYRROLIDINE; 3,4 DIETHYLIDENECYCLOPENTANE 1,1 DICARBOXYLIC ACID DIMETHYL ESTER; ALKENE; CATION; CYCLOPENTANE; DEUTERIODIMETHYL 3 BENZYLIDENE 4 METHYLCYCLOPENTANE 1,1 DICARBOXYLATE; DEUTERIUM; DIMETHYL 3 ETHYLIDENE 4 METHYLCYCLOPENTANE 1,1 DICARBOXYLATE; DIMETHYL 3 METHYL 4 METHYLENECYCLOPENTANE 1,1 DICARBOXYLATE; DIMETHYL 3,4 DIBENZYLIDENECYCLOPENTANE 1,1 DICARBOXYLATE; DIMETHYL 4 BENZYLIDENE 3,3 DIMETHYLCYCLOPENTANE 1,1 DICARBOXYLATE; HYDROGEN; METALLOCYCLOPENTADIENE; METALLOCYCLOPENTENE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBOCYCLIZATION; CHEMICAL BOND; CYCLIZATION; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; HYDROGENATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOISOMERISM;

EID: 3042597301     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048498i     Document Type: Article

References (65)

1. For a biographical sketch of Paul Sabatier, see: Lattes, A. C. R. Acad. Sci. Ser. IIc: Chim. 2000, 3, 705.
2. For a biographical sketch of Roger Adams, see: Tarbell, D. S.; Tarbell, A. T. J. Chem. Educ. 1979, 56, 163.
3. (a) Knowles, W. S. Prix Nobel 2001, 2002, 160.
4. (b) Knowles, W. S. Angew. Chem., Int. Ed. 2002, 41, 1998.
5. (c) Knowles, W. S. Adv. Synth. Catal. 2003, 345, 3.
6. (a) Noyori, R. Prix Nobel 2001, 2002, 186.
7. (b) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
8. (c) Noyori, R. Adv. Synth. Catal. 2003, 345, 15.
9. For catalytic C-C bond forming hydrogenations developed in our lab, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156.
10. (b) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143.
11. (c) Koech, P. K.; Krische, M. J. Org. Lett. 2004, 6, 691.
12. (d) Marriner, G. A.; Gamer, S. A.; Jang, H.-Y.; Krische, M. J. J. Org. Chem. 2004, 69, 1380.
13. (e) Jang, H.-Y.; Huddleston, R. R.; Krische, M. Angew. Chem., Int. Ed. 2003, 42, 4074.
14. (f) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4664.
15. (g) Huddleston, R. R.; Jang, H.-Y. Krische, M. J. J. Am. Chem. Soc. 2003, 125, 11488.
16. For a review on the heterolytic activation of elemental hydrogen, see: Brothers, P. J. Prog. Inorg. Chem. 1981, 28, 1,
17. Mild basic additives induce heterolytic activation of hydrogen via deprotonation of cationic rhodium dihydride intermediates: (a) Schrock, R. R.; Osbom, J. A. J. Am. Chem. Soc. 1976, 98, 2134.
18. (b) Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 2143.
19. (c) Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 4450.
20. For recent reviews on alkene hydroformylation, see: (a) Breit. B. Acc. Chem. Res. 2003, 36, 264.
21. (b) Breit, B.; Seiche, W. Synthesis 2001, 1.
22. For reviews on the Fischer-Tropsch reaction, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1982, 21, 117.
23. (b) Rofer-Depoorter, C.-K. Chem. Rev. 1981, 81, 447.
24. For reviews encompassing the metal-catalyzed cyclization of 1,6- and 1,7-diynes, see: (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996,96,635.
25. (b) Tamao, K.; Yamaguchi, S. Pure Appl Chem. 1996, 68, 139.
26. For metal-catalyzed cyclization of 1,6- and 1,7-diynes, see: (a) Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 110, 7255.
27. (b) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 6478.
28. (c) Trost, B. M.; Fleitz, F. J.; Watkins, W. J. J. Am. Chem. Soc. 1996, 110, 5146.
29. (d) Lautens, M.; Smith, N. D.; Ostrovsky, D. J. Org. Chem. 1997, 62, 8970.
30. (e) Onozawa, S.-Y.; Hatanaka, Y.; Tanaka, M. Chem. Commun. 1997, 1229.
31. (f) Onozawa, S.-Y.; Hatanaka, Y.; Choi, N.; Tanaka, M. Organometallics 1997, 16, 5389.
32. (g) Ojima, I.; Zhu, J.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690.
33. (h) Muraoka, T.; Matsuda, I.; Itoh, K. Tetrahedron Lett. 1998, 39, 7325.
34. (i) Gréau, S.; Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 2000, 122, 8579.
35. (j) Madine, J. W.; Wang, X.; Widenhoefer, R. A. Org. Lett. 2001, 3, 385.
36. (k) Wang, X.; Chakrapani, H.; Madine, J. W.; Keyerleber, M. A.; Widenhoefer, R. A. J. Org. Chem. 2002, 67, 2778.
37. (l) Muraoka, T.; Matsuda, I.; Itoh, K. Organometallics 2002, 21, 3650.
38. (m) Liu, C.; Widenhoefer, R. A. Organometallics 2002, 21, 5666.
39. (n) Uno, T.; Wakayanagi, S.; Sonoda, Y.; Yamamoto, K. Synlett 2003, 1997.
40. (o) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2003, 125, 11516.
41. For reviews encompassing the Pd-catalyzed cycloisomerization and reductive cyclization of 1,6-enynes, see: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
43. (c) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
44. (d) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
45. For selected examples of the cycloisomerization of 1,6-enynes catalyzed by metals other than palladium, see: (a) Titanium: Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121 1976.
46. (b) Rhodium: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490.
47. (c) Nickel-Chromium: Trost, B. M.; Tour, J. M. J. Am Chem. Soc, 1987, 109, 5268.
48. (d) Ruthenium: Nishida, M.; Adachi, N.; Onozuka, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158.
49. (e) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714.
50. (f) LaPaih, J.; Rodriguez, D. C.; Derien, S.; Dixneuf, P. H. Synlett 2000, 95.
51. (g) Cobalt: Ajamian, A.; Gleason, J. L. Org. Lett. 2003, 5, 2409.
52. (h) Iridium: Chatani, N.: Inoue, H.; Morimoto, T.; Muto, T.; Muria, S. J. Org. Chem. 2001, 66, 4433.
53. For a review of the acidity of metal hydrides, see: Norton, J. R. In Transition Metal Hydrides; Dedieu, A., Ed.; VCH Publishers: New York, 1992; Chapter 9.
54. For a review, see: Jung, M. E. Synlett 1999, 843.
55. (a) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2003, 125, 11516.
56. (b) Liu, C.; Widenhoefer, R. A. Organometallics 2002, 21, 5666.
57. (c) Padwa, A.; Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
58. (d) Son, S. U.; Park, K. H.; Lee, S. J.; Kim, B. M.; Chung, Y. K. Synth. Lett. 2003, 1101.
59. (e) Lucht, B. L.; Mao, S. S. H.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 4354.
60. (a) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782.
61. (b) Park, K. H.; Jung, I. G.; Kim, S. Y.; Chung, Y. K. Org. Lett, 2003, 5, 4967.
62. (c) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771.
63. (d) Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2003, 125, 11516.
64. (e) Buisine, O.; Aubert, C.; Malacria, M. Chem. Eur. J. 2001, 7, 3517.
65. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.