Rhodium(III)-catalyzed synthesis of isoquinolines from aryl ketone o -acyloxime derivatives and internal alkynes

Organic Letters

Volumn 12, Issue 24, 2010, Pages 5688-5691

  Too, Pei Chui ^a   Wang, Yi Feng ^a   Chiba, Shunsuke ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650350285     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102504b     Document Type: Article

References (47)

1. For recent reviews, see Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
2. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
3. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
4. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
5. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
6. Kulkarni, A. A.; Daugulis, O. Synthesis 2009, 4087
7. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
8. For selected reports on the ortho -metallation - 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
9. Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem., Int. Ed. 2009, 48, 2925
10. Kuninobu, Y.; Kikuchi, K.; Tokunaga, Y.; Nishina, Y.; Takai, K. Tetrahedron 2008, 64, 5974
11. Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202
12. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Org. Chem. 2005, 70, 6775
13. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229
14. Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687
15. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692
16. For utilization of 6p-electrocyclization of azatrienes generated by ortho -vinylation, see Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645
17. Yotphan, S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 2452
18. Parthasarathy, K.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2008, 10, 325
19. Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C.-H. Org. Lett. 2003, 5, 2759
20. Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
21. Fukutani, T.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Commun. 2009, 5141
22. For recent reports on ortho -metallation of aryloxime derivatives, see Sun, C.-L.; Liu, N.; Li, B.-J.; Yu, D.-G.; Wang, Y.; Shi, Z.-J. Org. Lett. 2010, 12, 184
23. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 9462
24. Yu, W.-Y.; Sit, W. N.; Lai, K.-M.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2008, 130, 3304
25. Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 126, 9048
26. Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542
27. For reports on Rh(III)-catalyzed oxidative C-H bond functionalization - C-N bond formation sequence triggered by amido and indole N-H bonds, see
28. Hyster, T. K.; Rovis, T. J. Am. Chem. Soc. 2010, 132, 10565
29. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
30. Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
31. Mochida, S.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2010, 39, 744
32. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
33. For a report on Rh(III)-catalyzed redox-neutral synthesis of isoquinolones from benzhydroxamic acid derivatives and alkynes, see
34. Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
35. For reports on Pd-catalyzed redox-neutral intramolecular aromatic C - H amination processes of O -acyloximes for the synthesis of indoles, see
36. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
37. Chiba, S.; Zhang, L.; Sanjaya, S.; Ang, G. Y. Tetrahedron 2010, 66, 5692
38. 3 did not work at all for the present process.
39. Li, L.; Brennessel, W. W.; Jones, W. D. Organometallics 2009, 28, 3492
40. Davies, D. L.; Al-Duaij, O.; Fawcett, J.; Giardiello, M.; Hilton, S. T.; Russell, D. R. Dalton Trans. 2003, 4132
41. All O -acetyloximes 1 in Table 2 were prepared from the corresponding ketones by treatment with hydroxylamine followed by acetylation of the resulting oximes. These processes could provide the desired anti stereochemistry as a sole/major isomer (see Supporting Information).
42. 6π-Electrocyclization was most likely ruled out from the possible reaction pathways by the reactions of ortho -alkenyloxime; see Supporting Information.
43. Li, L.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
44. Traynelis, V. J.; Pacini, P. L. J. Am. Chem. Soc. 1964, 86, 4917
45. For example, the reaction of Z -isomer of 1l provided only deacetylated oxime without formation of isoquinoline 3la; see Supporting Information.
46. For example, the reaction of isobutyrophenone with hydroxylamine provided an E, Z -mixture of oxime in an almost 1:1 ratio; see: Zhao, H.; Vandenbossche, C. P.; Koenig, S. G.; Singh, S. P.; Bakale, R. P. Org. Lett. 2008, 10, 505
47. Canonne, P.; Thibeault, D.; Fytas, G. Tetrahedron 1986, 42, 4203