Synthesis of azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes by Cu-Rh bimetallic relay catalysts

Journal of Organic Chemistry

Volumn 76, Issue 15, 2011, Pages 6159-6168

  Too, Pei Chui ^a   Chua, Sze Hui ^a   Wong, Siong Heng ^a   Chiba, Shunsuke ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL KETONES; AZA-HETEROCYCLES; BIMETALLIC SYSTEMS; CATALYTIC SYSTEM; INTERNAL ALKYNES; ISOQUINOLINES; PYRIDINE DERIVATIVES; SYN-ISOMERS; SYNTHETIC METHODS;

ACETYLENE; ISOMERS; KETONES; ORGANIC COMPOUNDS; PYRIDINE; RHODIUM COMPOUNDS;

RHODIUM;

ALKYNE; ARYL KETONE O ACETYL OXIME; AZAHETEROCYCLE; BETA CARBOLINE; COPPER; HETEROCYCLIC COMPOUND; ISOQUINOLINE DERIVATIVE; OXIME; PYRIDINE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ISOMER; SYNTHESIS;

ALKYNES; CARBOLINES; CATALYSIS; COPPER; HETEROCYCLIC COMPOUNDS; ISOQUINOLINES; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIMES; PYRIMIDINES; RHODIUM;

EID: 79961044232     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200897q     Document Type: Article

References (78)

1. For recent reviews, see: Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Elsevier: Oxford, 2008; Vol. 20 and others in this series.
2. Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon: Oxford, 2008.
3. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon: Oxford, 2008.
4. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., McKillop, A., Eds.; Pergamon: Oxford, 1996, and references therein.
5. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles; Wiley-VCH: Weinheim, 2003.
6. For recent reviews, see: Ackermann, L. Chem. Rev. 2011, 111, 1315
7. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212
8. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
9. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
10. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
11. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
12. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
13. Kulkarni, A. A.; Daugulis, O. Synthesis 2009, 4087
14. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
15. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222
16. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077
17. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731
18. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826
19. Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698
20. For selected reports on the ortho metalation/C-C bond formation sequence of aldimine and ketimine derivatives, see: Gao, K.; Lee, P.-S.; Fujita, T.; Yoshikai, N. J. Am. Chem. Soc. 2010, 132, 12249
21. Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925
22. Kuninobu, Y.; Nishina, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2008, 130, 14062
23. Kuninobu, Y.; Kikuchi, K.; Tokunaga, Y.; Nishina, Y.; Takai, K. Tetrahedron 2008, 64, 5974
24. Kuninobu, Y.; Nishina, Y.; Nakagawa, C.; Takai, K. J. Am. Chem. Soc. 2006, 128, 12376
25. Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202
26. Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498
27. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2005, 70, 6775
28. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229
29. Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687
30. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692
31. Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K.-Y. Angew. Chem., Int. Ed. 2000, 39, 3440
32. Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 1053
33. Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647
34. Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111
35. For utilization of 6π-electrocyclization of azatrienes generated by ortho vinylation, see: Parthasarathy, K.; Cheng, C.-H. J. Org. Chem. 2009, 74, 9359
36. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645
37. Yotphan, S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 2452
38. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2008, 10, 325
39. Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C.-H. Org. Lett. 2003, 5, 2759
40. Davies, D. L.; Al-Duaij, O.; Fawcett, J.; Giardiello, M.; Hilton, S. T.; Russell, D. R. Dalton Trans. 2003, 4132
41. Li, L.; Brennessel, W. W.; Jones, W. D. Organometallics 2009, 28, 3492
42. For report on stoichiometric use of Rh(III) for synthesis of isoquinolines, see: Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414 For reports on Rh(III)-catalyzed oxidative C-H bond functionalization/C-N bond formation with alkynes, see: Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326
43. Chen, J.; Song, G.; Pan, C.-L.; Li, X. Org. Lett. 2010, 12, 5426
44. Su, Y.; Zhao, M.; Han, K.; Song, G.; Li, X. Org. Lett. 2010, 12, 5462
45. Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565
46. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
47. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
48. Mochida, S.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2010, 39, 744
49. Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
50. Fukutani, T.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Commun. 2009, 5141
51. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
52. For a review, see: Patureau, F. W.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1977
53. For a report on Rh(III)-catalyzed redox-neutral synthesis of azaheterocycles from benzhydroxamic acid derivatives and oxime derivatives with alkynes, see: Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
54. Too, P. C.; Wang, Y.-F.; Chiba, S. Org. Lett. 2010, 12, 5688
55. Zhang, X.; Chen, D.; Zhao, M.; Zhao, J.; Jia, A.; Li, X. Adv. Synth. Catal. 2011, 353, 719
56. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
57. Gerfaund, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2009, 48, 572
58. Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 4505
59. Sakoda, K.; Mihara, J.; Ichikawa, J. Chem. Commun. 2005, 4684
60. Kitamura, M.; Narasaka, K. Chem. Rec. 2002, 2, 268
61. Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2000, 122, 12049
62. Liu, S.; Liebeskind, L. S. J. Am. Chem. Soc. 2008, 130, 6918
63. Liu, S.; Yu, Y.; Liebeskind, L. S. Org. Lett. 2007, 9, 1947
64. For reports on one-electron reduction of O -acyloximes by Cu(I) complexes, see: Tanaka, K.; Kitamura, M.; Narasaka, K. Bull. Chem. Soc. Jpn. 2005, 78, 1659
65. Koganemaru, Y.; Kitamura, M.; Narasaka, K. Chem. Lett. 2002, 784
66. Kim, J.; Chang, S. J. Am. Chem. Soc. 2010, 132, 10272
67. Malkhasian, A. Y. S.; Finch, M. E.; Nikolovski, B.; Menon, A.; Kucera, B. E.; Chavez, F. A. Inorg. Chem. 2007, 46, 2950
68. Teo, J. J.; Chang, Y.; Zeng, H. C. Langmuir 2006, 22, 7369
69. For reports on formation of carbonitriles from O -acetylaldoximes, see: Raffaelli, A.; Rosini, C.; Dini, M.; Salvadori, P. Synthesis 1988, 893
70. Marvel, C. S.; Miller, W. R.; Chou, L. C. J. Am. Chem. Soc. 1950, 72, 5408
71. Mowry, D. T.; Morner, R. R. J. Am. Chem. Soc. 1947, 69, 1831
72. Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L.; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A. Org. Lett. 2002, 4, 3199
73. Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076
74. Wang, C.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006
75. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
76. Schmink, J. R.; Leadbeater, N. E. Org. Lett. 2009, 11, 2575
77. Song, C.; Knight, D. W.; Whatton (neé Fagan), M. A. Tetrahedron Lett. 2004, 45, 9573
78. Akimoto, H.; Kawai, A.; Nomura, H. Bull. Chem. Soc. Jpn. 1985, 58, 123