The first regioselective hydroformylation of acetylenic thiophenes catalyzed by a zwitterionic rhodium complex and triphenyl phosphite

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9640-9645

  Van Den Hoven, Bernard G ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALDEHYDE; BENZENE DERIVATIVE; RHODIUM DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033601245     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912653     Document Type: Article

References (63)

1. (a) Dubois, M. R. Chem. Rev. 1989, 89, 1.
2. (b) Hegedus, L. L.; McCabe, R. W. In Catalyst Poisoning; Marcel Dekker: New York, 1984.
3. (c) Hutton, A. T. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, 1984; Vol. 5, p 1151.
4. (a) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman and Hall: London, 1995.
5. (b) Meyers, A. I. In Heterocycles in Organic Chemistry; Taylor, E.C., Weissberger, A., Eds.; John Wiley and Sons: New York, 1974.
6. (c) Paquette, L. A. Principles of Modern Heterocyclic Chemistry, W. A. Benjamin Inc.: New York, 1968.
7. (a) Krohn, K., Kirst, H. A., Maag, H., Eds. Antibiotics and Antivirial Compounds; VCH Publishers Inc.: New York, 1993.
8. (b) Lednicer, D.; Mitscher, L. A. Organic Chemistry of Drug Synthesis; John Wiley and Sons: New York, 1977.
9. (a) Choi, W.; Sanda, F.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 1189.
10. (b) Ng, S. C.; Chan, H. S. O.; Wong, P. M. L.; Tan, K. L.; Tanb, B. T. G. Polymer 1998, 39, 4963.
11. (c) Longridge, J. J.; Rawson, J. M. Polyhedron 1998, 17, 1871.
12. Aldea, R.; Alper, H. J. Org. Chem. 1995, 60, 8365.
13. Khumtaveeporn, K.; Alper, H. J. Am. Chem. Soc. 1994, 116, 5662.
14. (a) Xiao, W.-J.; Alper, H. J. Org. Chem. 1997, 62, 3422.
15. (b) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609.
16. (c) Xiao, W.-J..; Alper, H. J. Org. Chem. 1998, 63, 7939.
17. (d) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1999, 64, 2080.
18. (a) Totland, K.; Alper, H. J. Org. Chem. 1993, 58, 3326.
19. (b) Alper, H.; Zhou, J. Q. J. Org. Chem. 1992, 57, 3729.
20. (c) Amer, I.; Alper, H. J. Am. Chem. Soc. 1990, 112, 3674.
21. (d) Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499.
22. Johnson, J. R.; Cuny, G. D.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1760.
23. Ishii, Y.; Miyashita, K.; Kamita, K.; Hidai, M. J. Am. Chem. Soc. 1997, 119, 6448.
24. Van den Hoven, B. G.; Alper, H. J. Org. Chem. 1999, 64, 3964.
25. Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry II; Pergamon: Oxford, 1996; Vol. 2, p 679.
26. (a) Carpita, A.; Lezzi, A.; Rossi, R.; Marchetti, F.; Merlino, S. Tetrahedron 1985, 41, 621.
27. (b) Rossi, R.; Carpita, A.; Lezzi, A. Tetrahedron 1984, 40, 2773.
28. (c) Sakamoto, T.; Shiraiwa, M.; Kondo, Y.; Yamanaka, H. Synthesis 1983, 312.
29. (d) Ames, D. E.; Bull, D.; Takundwa, C. Synthesis 1981, 364.
30. (e) D'Auria, M.; De Mico, A.; D'Onofrio, F.; Piancatelli, G. J. Org. Chem. 1987, 52, 5243.
31. (a) Boivin, J.; Huppe, S.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 8735.
32. (b) Degl'Innocenti, A.; Funicello, M.; Scafato, P.; Spagnolo, P. Tetrahedron Lett. 1997, 38, 2171.
33. (c) Varney, M. D.; Rommes, W. H.; Palmer, C. L. PCT Int. Appl. WO 9,640,674, 1996.
34. (d) Tanaka, H.; Fukuzumi, K.; Togawa, T.; Banno, K.; Ushiro, T.; Morii, M.; Nakatani, T. PCT Int. Appl. WO 9,633,195, 1996.
35. (e) Chan, M. F.; Raju, B. G.; Kois, A.; Verner, E. J.; Wu, C.; Castillo, R. S.; Yalamoori, V.; Balaji, V. N. US Patent 5,594,021, 1997.
36. (f) Labadie, S. S. Synth. Commun. 1998, 28, 2531.
37. (a) Li, Y.; Thiemann, T.; Sawada, T.; Mataka, S.; Tashiro, M. J. Org. Chem. 1997, 62, 7926.
38. (b) Katritzky, A. R.; Serdyuk, L.; Xie, L.; Ghiviriga, I. J. Org. Chem. 1997, 62, 6215.
39. (c) Hoerndler, C.; Hansen, H. J. Helv. Chim. Acta 1997, 80, 2520.
40. (d) Kaye, P. T.; Molema, W. E. Chem. Commun. 1998, 2479.
41. (e) Cossy, J.; Rakotoarisoa, H.; Kahn, P.; Desmurs, J.-R. Tetrahedron Lett. 1998, 39, 9671.
42. (f) Jones, R. C. F.; Patel, P.; Hirst, S. C.; Smallridge, M. J. Tetrahedron 1998, 54, 6191.
43. (g) Höppe, H. A., Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Walsh, K. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 1545.
44. (a) Boldi, A. M.; Johnson, C. R.; Eissa, H. O. Tetrahedron Lett. 1999, 40, 619.
45. (b) Lu, T.-J.; Cheng, S.-M.; Sheu, L.-J. J. Org. Chem. 1998, 63, 2738.
46. (c) Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234.
47. (d) Yoshimatsu, M.; Oguri, K., Ikeda, K.; Gotoh, S. J. Org. Chem. 1998, 63, 4475.
48. (a) Chang, C.-T.; Chen, K.-M.; Liu, W.-H.; Lin, F.-I.; Wu, R.-T., U.S. Patent 5,602,170, 1997.
49. (b) Chang, C.-T.; Chen, K.-M.; Liu, W.-H.; Lin, F.-I., Wu, R.-T. U.S. Patent 5,747,525, 1998.
50. (c) Ebermann, R.; Alth, G.; Kreitner, M.; Kubin, A. J. Photochem. Photobiol., B 1996, 36, 95.
51. (d) Wierzbicky, M.; Sauveur, F.; Bonnet, J.; Tordjman, C. Fr. Demande FR 2,752,576, 1998.
52. (e) Asari, T.; Okamoto, S.; Kono, S. Japanese Patent 10,316, 673, 1998.
53. (a) Walter, H. PCT Int. Appl. WO 9,733,890, 1997.
54. (b) Morita, K.; Murabayashi, A., Japanese Patent 09,095,482, 1997.
55. (c) Kanehira, K.; Tagawa, H.; Shiono, M. Japanese Patent 09,104,682, 1997.
56. (d) Fischer, R.; Dumas, J.; Bretschneider, T.; Gallenkamp, B.; Lieb, F.; Wernthaler, K.; Erdelen, C.; Wachendorff-Neumann, U.; Mencke, N.; Turberg, A. Ger. Offen DE 19,527,190,1996.
57. (e) Theobald, H.; Harries, V.; Kardorff, U.; Baeuerle, P.; Goetz, G. PCT Int. Appl. WO 9,314,079, 1993.
58. Sargent, A. L.; Titus, E. P. Organometallics 1998, 17, 65.
59. (a) Doyama, K.; Job, T.; Takahashi, S. Tetrahedron. Lett. 1996, 27, 4497.
60. (b) Doyama, K.; Joh, T.; Shiohara, T.; Takahashi, S. Bull. Chem. Soc. Jpn. 1988, 61, 4353.
61. (c) Campi, E. M.; Jackson, W. R. Aust. J. Chem. 1989, 42, 471.
62. Gaeriner, R. J. Am. Chem. Soc. 1952, 74, 4950.
63. Schrock, P. R.; Osborn, J. A. Inorg. Chem. 1970, 9, 2339.