Progress in carbonylative [2+2+1] cycloaddition: Utilization of a nitrile group as the πa component

Angewandte Chemie - International Edition

Volumn 52, Issue 42, 2013, Pages 11138-11142

  Iwata, Takashi ^a   Inagaki, Fuyuhiko ^a   Mukai, Chisato ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

allenes; cycloaddition; heterocycles; rhodium; synthetic methods

Indexed keywords

ALLENES; CATALYTIC AMOUNTS; CO ATMOSPHERE; HETEROCYCLES; NITRILE GROUPS; PHENYLACETONITRILE; SYNTHETIC METHODS;

CHEMICAL REACTIONS; CYCLOADDITION; RHODIUM;

CHEMISTRY;

ALKADIENE; NITRILE; RHODIUM;

ALLENES; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; HETEROCYCLES; SYNTHETIC METHODS;

ALLENES; CYCLOADDITION; HETEROCYCLES; RHODIUM; SYNTHETIC METHODS;

ALKADIENES; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; NITRILES;

EID: 84885460825     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201305729     Document Type: Article

References (60)

1. I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, J. Chem. Soc. Chem. Commun. 1971, 36.
2. E. Negishi, D. Choueiry, T. B. Nguyen, D. R. Swanson, N. Suzuki, T. Takahashi, J. Am. Chem. Soc. 1994, 116, 9751-9752
3. P. A. Wender, M. P. Croatt, N. M. Deschamps, J. Am. Chem. Soc. 2004, 126, 5948-5949
4. T. Makino, K. Itoh, J. Org. Chem. 2004, 69, 395-405
5. F. Inagaki, C. Mukai, Org. Lett. 2006, 8, 1217-1220.
6. N. M. Kablaoui, F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 5818-5819
7. N. M. Kablaoui, F. A. Hicks, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 4424-4431
8. N. Chatani, M. Tobisu, T. Asaumi, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1999, 121, 7160-7161
9. M. Tobisu, N. Chatani, T. Asaumi, K. Amako, Y. Ie, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 2000, 122, 12663-12674
10. S. K. Mandal, S. R. Amin, W. E. Crowe, J. Am. Chem. Soc. 2001, 123, 6457-6458
11. N. Chatani, Chem. Rec. 2008, 8, 201-212
12. D. F. Finnegan, M. L. Snapper, J. Org. Chem. 2011, 76, 3644-3653.
13. W. E. Crowe, A. T. Vu, J. Am. Chem. Soc. 1996, 118, 1557-1558
14. N. Chatani, T. Morimoto, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1998, 120, 5335-5336
15. S.-K. Kang, K.-J. Kim, Y.-T. Hong, Angew. Chem. 2002, 114, 1654-1656
16. Angew. Chem. Int. Ed. 2002, 41, 1584-1586
17. C.-M. Yu, Y.-T. Hong, J.-H. Lee, Synlett 2004, 1695-1698
18. C.-M. Yu, Y.-T. Hong, J.-H. Lee, J. Org. Chem. 2004, 69, 8506-8509
19. S. Ogoshi, M. Oka, H. Kurosawa, J. Am. Chem. Soc. 2004, 126, 11802-11803
20. J. Adrio, J. C. Carretero, J. Am. Chem. Soc. 2007, 129, 778-779
21. P. Gao, P.-F. Xu, H. Zhai, J. Org. Chem. 2009, 74, 2592-2593
22. J. Chen, P. Gao, F. Yu, Y. Yang, S. Zhu, H. Zhai, Angew. Chem. 2012, 124, 5999-6001
23. Angew. Chem. Int. Ed. 2012, 51, 5897-5899.
24. N. Chatani, T. Morimoto, A. Kamitani, Y. Fukumoto, S. Murai, J. Organomet. Chem. 1999, 579, 177-181
25. N. Chatani, M. Tobisu, T. Asaumi, K. Amako, Y. Ie, Y. Fukumoto, S. Murai, Synthesis 2000, 925-928
26. A. Göbel, W. Imhof, Chem. Commun. 2001, 593-594.
27. T. Saito, M. Siotani, T. Otani, S. Hasaba, Heterocycles 2003, 60, 1045-1048
28. C. Mukai, T. Yosida, M. Sorimachi, A. Odani, Org. Lett. 2006, 8, 83-86
29. T. Saito, K. Sugizaki, T. Otani, T. Suyama, Org. Lett. 2007, 9, 1239-1241
30. D. Aburano, T. Yoshida, N. Miyakoshi, C. Mukai, J. Org. Chem. 2007, 72, 6878-6884
31. T. Saito, H. Nihei, T. Otani, T. Suyama, N. Furukawa, Chem. Commun. 2008, 172-174
32. T. Saito, N. Furukawa, T. Otani, Org. Biomol. Chem. 2010, 8, 1126-1132.
33. J. A. Varela, C. Saá, Chem. Rev. 2003, 103, 3787-3802
34. B. Heller, M. Hapke, Chem. Soc. Rev. 2007, 36, 1085-1094
35. J. A. Varela, C. Saá, Synlett 2008, 2571-2578
36. K. Tanaka, Heterocycles 2012, 85, 1017-1043; For selected examples of rhodium-catalyzed [2+2+2] cycloaddition with nitriles, see
37. P. Cioni, P. Diversi, G. Ingrosso, A. Lucherini, P. Ronca, J. Mol. Catal. 1987, 40, 337-357
38. P. Diversi, G. Ingrosso, A. Lucherini, A. Minutillo, J. Mol. Catal. 1987, 40, 359-377
39. P. Diversi, L. Ermini, G. Ingrosso, A. Lucherini, J. Organomet. Chem. 1993, 447, 291-298
40. K. Tanaka, N. Suzuki, G. Nishida, Eur. J. Org. Chem. 2006, 3917-3922
41. A. Wada, K. Noguchi, M. Hirano, K. Tanaka, Org. Lett. 2007, 9, 1295-1298
42. K. Tanaka, H. Hara, G. Nishida, M. Hirano, Org. Lett. 2007, 9, 1907-1910
43. T. Shibata, T. Uchiyama, K. Endo, Org. Lett. 2009, 11, 3906-3908
44. Y. Komine, K. Tanaka, Org. Lett. 2010, 12, 1312-1315; Nickel-catalyzed [4+2] cycloaddition with nitriles is also reported. See
45. M. Ohashi, I. Takeda, M. Ikawa, S. Ogoshi, J. Am. Chem. Soc. 2011, 133, 18018-18021.
46. F. Inagaki, S. Kitagaki, C. Mukai, Synlett 2011, 594-614, and references therein
47. M. T. S. Shafawati, F. Inagaki, T. Kawamura, C. Mukai, Tetrahedron 2013, 69, 1509-1515.
48. F. Inagaki, K. Sugikubo, Y. Miyashita, C. Mukai, Angew. Chem. 2010, 122, 2252-2256
49. Angew. Chem. Int. Ed. 2010, 49, 2206-2210
50. F. Inagaki, K. Sugikubo, Y. Oura, C. Mukai, Chem. Eur. J. 2011, 17, 9062-9065
51. C. Mukai, Y. Ohta, Y. Oura, Y. Kawaguchi, F. Inagaki, J. Am. Chem. Soc. 2012, 134, 19580-19583.
52. 6] was shown to be effective for our purpose and only a complex mixture was formed. It has already been shown that the rhodium(I)-catalyzed PKTR of enynes under a low CO pressure occasionally provides better results (see, F. Inagaki, N. Itoh, Y. Hayashi, Y. Matsui, C. Mukai, Beilstein J. Org. Chem. 2011, 7, 404-409). Thus, we next examined the effect of the CO pressure, but a yield better than 60 % yield could not be achieved.
53. C. Nahera, M. Yus, Tetrahedron 1999, 55, 10547-10658.
54. S. Kitagaki, K. Ohdachi, K. Katoh, C. Mukai, Org. Lett. 2006, 8, 95-98
55. S. Kitagaki, Y. Okumura, C. Mukai, Tetrahedron Lett. 2006, 47, 1849-1852
56. S. Kitagaki, K. Katoh, K. Ohdachi, Y. Takahashi, D. Shibata, C. Mukai, J. Org. Chem. 2006, 71, 6908-6914
57. S. Kitagaki, Y. Okumura, C. Mukai, Tetrahedron 2006, 62, 10311-10320.
58. A. Padwa, P. E. Yeske, J. Am. Chem. Soc. 1988, 110, 1617-1618
59. A. Padwa, P. E. Yeske, J. Org. Chem. 1991, 56, 6386-6390
60. The oxyindole derivative 18 was tentatively regarded as an over-oxidized product of 17. Thus, the compound 17 was exposed to the rhodium(I) catalyst under the standard reaction conditions, but no conversion into 18 could be observed and 17 was recovered intact.