Carbopalladation of nitriles: Synthesis of benzocyclic ketones and cyclopentenones via Pd-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles and related compounds

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9428-9438

  Pletnev, Alexandre A ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INTERMOLECULAR CARBOPALLADATIONS;

KETONES; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

BENZOCYCLIC KETONE; CYCLOPENTENONE; INDANONE DERIVATIVE; KETONE DERIVATIVE; NITRILE; PALLADIUM; PROPANENITRILE; TETRALONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; METHODOLOGY; SYNTHESIS;

EID: 0037184890     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0262006     Document Type: Article

References (77)

1. (a) Bhattacharya, A.; Segmuller, B.; Ybarra, A. Synth. Commun. 1996, 26, 1775.
2. (b) Smonou, I.; Orfanopoulos, M. Synth. Commun. 1990, 20, 1387.
3. (c) Witiak, D. T.; Williams, D. R.; Kakodkar, S. V. J. Org. Chem. 1974, 39, 1242.
4. (d) Gutman, A. L.; Etinger, M.; Nisnevich, G.; Polyak, F. Tetrahedron: Asymmetry 1998, 9, 4369.
5. Galatsis, P.; Manwell, J. J.; Blackwell, J. M. Can. J. Chem. 1994, 72, 1656.
6. (a) Sartori, G.; Maggi, R.; Bigi, F.; Porta, C.; Tao, X.; Bernardi, G. L.; Ianelli, S.; Nardelli, M. Tetrahedron 1995, 51, 12179.
7. (b) Watanabe, M.; Morimoto, H.; Tomoda, M.; Iwanaa, U. Synthesis 1994, 1083.
8. (a) Lin, S.-K.; Rasetti, V. Helv. Chim. Acta 1995, 78, 857.
9. (b) Johansson, A. M.; Mellin, C.; Hacksell, U. J. Org. Chem. 1986, 51, 5252.
10. (c) Harvey, A. L.; MacTavish, J.; Mullins, S. J.; Proctor, G. R. J. Chem. Res., Synop. 1997, 420.
11. (a) Yang, F. Z.; Trost, M. K.; Fristad, W. E. Tetrahedron Lett. 1987, 28, 1493.
12. (b) Esteban, G.; Lopez-Sanchez, M. A.; Martinez, M.; Plumet, J. Tetrahedron 1998, 54, 197.
13. (a) Ishii, H.; Chen, I.-S.; Ueki, S.; Masuda, T.; Morita, K.; Ishikawa, T. J. Chem. Soc., Perkin Trans. 1 1987, 2415.
14. (b) Vicario, J. L.; Badia, D.; Dominguez, E.; Carrillo, L. Tetrahedron: Asymmetry 2000, 11, 1227.
15. (c) Yoshida, M.; Watanabe, T.; Ishikawa, T. Heterocycles 2001, 54, 433.
16. Patil, M. L.; Borate, H. B.; Ponde, D. E.; Bhawal, B. M.; Deshpande, V. H. Tetrahedron Lett. 1999, 40, 4437.
17. Liard, A.; Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 1759.
18. (a) Johnson, W. S. Org. React. 1944, 2, 114.
19. (b) Sangaiah, R.; Gold, A. J. Org. Chem. 1991, 56, 6717.
20. (c) Carpino, L. A.; Lin, Y.-Z. J. Org. Chem. 1990, 55, 247.
21. (a) Bruson, H. A.; Plant, H. L. J. Org. Chem. 1967, 32, 3356.
22. (b) Doyama, K.; Fujiwara, K.; Joh, T.; Maeshima, K.; Takahashi, S. Chem. Lett. 1988, 901.
23. (a) Henin, F.; M'Boungou-M'Passi, A.; Muzart, J.; Pete, J.-P. Tetrahedron 1994, 50, 2849.
24. (b) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061.
25. (a) Borg, R. M.; Berry, M. A.; Mangion, D. Tetrahedron Lett. 1994, 35, 8485.
26. (b) Pinnick, H. W.; Brown, S. P.; McLean, E. A.; Zoller, R. W., III J. Org. Chem. 1981, 46, 3758.
27. Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238.
28. For a preliminary communication, see: Pletnev, A. A.; Larock, R. C. Tetrahedron Lett. 2002, 43, 2133.
29. Similar reaction conditions were found to induce nitrile carbo-palladation previously, see: (a) Yang, C.-C.; Tai, H.-M.; Sun, P.-J. J. Chem. Soc., Perkin Trans. 1 1997, 2843.
30. (b) Deng, J.-H.; Tai, H.-M.; Yang, C.-C. J. Chin. Chem. Soc. 2000, 47, 327.
31. (a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827.
32. (b) Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619.
33. Cyclization of the corresponding aryl bromide was found to be ineffective, producing mostly the reduction byproduct and only trace amounts of 2a.
34. 2, with the latter further reacting with water to afford ammonia and IPdOH or an equivalent Pd(II) species. Alternatively, reaction of the iminopalladium intermediate with water may lead directly to IPdOH and the indanone imine, which is then hydrolyzed to I.
35. Pletnev, A. A.; Tian, Q.; Larock, R. C. J. Org. Chem. 2002, 68, 9276.
36. This reduction presumably proceeds via oxidative addition of the α-C-H bond of triethylamine to Pd, followed by fragmentation of the resulting species, See also: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571 and references therein. (b) Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348. (c) Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429.
37. This reduction presumably proceeds via oxidative addition of the α-C-H bond of triethylamine to Pd, followed by fragmentation of the resulting species, See also: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571 and references therein. (b) Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348. (c) Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429.
38. This reduction presumably proceeds via oxidative addition of the α-C-H bond of triethylamine to Pd, followed by fragmentation of the resulting species, See also: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571 and references therein. (b) Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348. (c) Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429.
39. For an example of such a process, see: Qabaja, G.; Jones, G. B. J. Org. Chem. 2000, 65, 7187.
40. (a) Larock, R. C. Comprehensive Organic Transformations, 2nd Ed.; Wiley-VCH: New York, 1999; p 1542.
41. (b) Larock, R. C. Comprehensive Organic Transformations, 2nd Ed.; Wiley-VCH: New York, 1999; p 571.
42. 2, 1s) [from: Jaffe, H. H. Chem. Rev. 1953, 53, 191].
43. (a) Tsuji, J.; Mandai, T. Synthesis 1996, 1 and references therein.
44. (b) Cacchi, S.; Felici, M.; Pietroni, B. Tetrahedron Lett. 1984, 25, 3137.
45. (a) Larock, R. C.; Yum, E. K. Tetrahedron 1996, 52, 2743.
46. (b) Balme, G.; Fouret, G.; Gore, J. Tetrahedron Lett. 1986, 27, 3855.
47. (c) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4450.
48. (a) Satoh, T.; Yoshida, M.; Ota, H. Tetrahedron Lett. 2001, 42, 9241.
49. (b) Hailes, H. C.; Isaac, B.; Javaid, M. H. Tetrahedron Lett. 2001, 42, 7325.
50. (c) Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429.
51. (d) Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis 1994, 867.
52. (a) Miler, J. A.; Pugh, A. W.; Ullah, G. M.; Welsh, G. M. Tetrahedron Lett. 2001, 42, 955.
53. (b) Trost, B. M.; Pinkerton, A. B. J. Org. Chem. 2001, 66, 7714.
54. Ellison, F. A. Synthesis 1973, 397.
55. Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857.
56. (a) Schore, N. E. Org. React. 1991, 40, 1.
57. (b) Krafft, M. E.; Bonaga, L. V. R.; Hirosawa, C. J. Org. Chem. 2001, 66, 3004.
58. Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5881.
59. Ranu, B. C.; Jana, U. J. Org. Chem. 1999, 64, 6380.
60. Mori, M.; Kaneta, N.; Shibasaki, M. J. Organomet. Chem. 1994, 464, 35.
61. Orliac-Le Moing, A.; Delaunay, J.; Lebouc, A.; Simonet, J. Tetrahedron 1985, 41, 4483.
62. (a) Klumpp, D. A.; Lau, S.; Garza, M.; Schick, B.; Kantardjieff, K. J. Org. Chem. 1999, 64, 7635.
63. (b) Beringer, F. M.; Daniel, W. J.; Galton, S. A.; Rubin, G. J. Org. Chem. 1966, 31, 4315.
64. Suzuki, T.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1997, 119, 6774.
65. Berner, D.; Cox, D. P.; Dahn, H. Helv. Chim. Acta 1982, 65, 2061.
66. Cawley, J. J.; Petrocine, D. V. J. Org. Chem. 1976, 41, 2608.
67. Dolbier, W. R., Jr.; Matsui, K.; McCullagh, L.; Anapolle, K. E. J. Org. Chem. 1979, 44, 2842.
68. Enas, J. D.; Garcia, J. G.; Mathis, C. A.; Gerdes, J. M. J. Fluorine Chem. 1993, 63, 233.
69. 1H NMR spectrum of an authentic sample obtained from Aldrich Chemical Co., Inc.
70. (a) Farcasiu, D.; Schlosberg, R. H. J. Org. Chem. 1982, 47, 151.
71. (b) Burdon, M. G.; Moffatt, J. G. J. Am. Chem. Soc. 1966, 88, 5855.
72. Moncovic, I.; Wong, H.; Belleau, B.; Pachter, I. J.; Perron, Y. G. Can. J. Chem. 1975, 53, 2515.
73. Dunkelblum, E.; Hart, H.; Suzuki, M. J. Am. Chem. Soc. 1977, 99, 5074.
74. Prempree, P.; Siwapinyoyos, T.; Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron Lett. 1980, 21, 1169.
75. Iwasawa, N.; Matsuo, T.; Iwamoto, M.; Ikeno, T. J. Am. Chem. Soc. 1998, 120, 3903.
76. (a) Umemura, K.; Matsuyama, H.; Watanabe, N.; Kobayashi, M.; Kamigata, N. J. Org. Chem. 1989, 54, 2374.
77. (b) Marshall, P. A.; Prager, R. H. Aust. J. Chem. 1979, 32, 1261.