Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by α-aryldiazoesters

Organic Letters

Volumn 12, Issue 3, 2010, Pages 604-607

  Chan, Wai Wing ^a   Yeung, Shing Hin ^a   Zhou, Zhongyuan ^a   Chan, Albert S C ^a   Yu, Wing Yiu ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLES; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 75749128563     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9028226     Document Type: Article

References (60)

1. For comprehensive reviews, see:
2. (a) Doyle, M.; Mckervey, M.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; John Wiley & Sons Inc.: New York, 1998. For recent reviews on Rh-catalyzed carbenoid C-H insertion reactions, see:
3. (b) Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. DOI: 10.1021/cr900239n. Published Online: Sept 28, 2009 (Review),
4. (c)Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
5. (d)Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
6. (a) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
7. (b) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
8. (c)Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
9. (d)Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199.
10. (e) Sundberg, R. J. Indoles; Academic Press: London, UK, 1996.
11. (f) Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
12. (a) Becclalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
13. (b) Zeni, G.; Larcok, R. C. Chem. Rev. 2006, 106, 4644.
14. (c)Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 42, 4257.
15. (d)van Esseveldt, B. C J.; van Delft, F. L.; de Geld, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717.
16. (a) Gibe, R.; Kerr, M. A. J. Org. Chem. 2002, 67, 6247.
17. (b) Antos, J. M.; Francis, M. B. J. Am. Chem. Soc. 2004, 126, 10256.
18. (c)Hedley, S. J.; Ventura, D. L.; Dominiak, P. M.; Nygren, C. L.; Davies, H. M. L. J. Org. Chem. 2006, 71, 5349.
19. (a) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
20. (b) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
21. For a review, see: Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
22. (a) Yu, W.-Y.; Sit, W. N.; Zhou, Z.; Chan, A. S.-C. Org. Lett. 2009, 11, 3174.
23. (b) Yu, W.-Y.; Tai, Y.-T.; Zhou, Z.; Chan, A. S. C. Org. Lett. 2009, 11, 469.
24. (c)Yu, W.-Y.; Sit, W. N.; Lai, K.-M.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2008, 130, 3304.
25. (d)Thu, H.-Y.; Yu, W.-Y.; Che, C-M. J. Am. Chem. Soc. 2006, 128, 9048.
26. (e) Choi, M. K.-W.; Yu, W.-Y.; Che, C-M. Org. Lett. 2005, 7, 1081.
27. (f) Cheung, W.-H.; Zheng, S.-L.; Yu, W.-Y.; Zhou, G.-C.; Che, C.-M. Org. Lett. 2003, 5, 2535.
28. For selected examples of C3-selective alkylations of indoles, see:
29. (a) Hong, L.; Wang, L.; Chen, C.; Zhang, B.; Wang, R. Adv. Synth. Catal. 2009, 351, 111.
30. (b) Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593.
31. (c)Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem., Int. Ed. 2008, 47, 4061.
32. (d)Dong, H.-M.; Lu, H.-H.; Lu, L.-Q.; Chen, C.-B.; Xiao, W.-J. Adv. Synth. Catal. 2007, 349, 1597.
33. (e) Chen, W.; Du, W.; Yue, L.; Li, R.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Org. Biomol. Chem. 2007, 5, 816.
34. (f) Blay, G.; Fernández, I.; Pedro, J. R.; Vila, C. Org. Lett. 2007, 9, 2601.
35. (g) Yang, H.; Hong, Y.-T.; Kim, S. Org. Lett. 2007, 9, 2281.
36. (h) Li, C.-F.; Liu, H.; Liao, J.; Cao, Y.-J.; Liu, X.-P.; Xiao, W.-J. Org. Lett. 2007, 9, 1874.
37. Bartoli, G.; Bosco, M.; Carlone, A.; Pesciaioli, F.; Sambri, L.; Melchiorre, P. Org. Lett. 2007, 9, 1403.
38. For C2 arylation of indoles, see:
39. (a) Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673.
40. (b) Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
41. (c)Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926.
42. (d)Wang, X.; Gribkov, D. V.; Sames, D. J. Org. Chem. 2007, 72, 1476.
43. (e) Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072.
44. (f) Toure, B. B.; Lane, B. S.; Sames, D. Org. Lett. 2006, 8, 1979.
45. (g) Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
46. (h) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274. For C2 alkenylation of indoles, see:
47. (i)García-Rubia, A.; Arrayas, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48-6511.
48. (j) Maehara, A.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1159.
49. (k) Capito, E.; Brown, J. M.; Ricci, A. Chem. Commun. 2005, 1854.
50. Grimster, N.P.; Guantlett, C.; Godfrey, C.R.A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 4, 3125.
51. Deng, Q.-H.; Xu, H.-W.; Yuen, A. W.-H.; Xu, Z.-J.; Che, C.-M. Org. Lett. 2008, 10, 1529.
52. (a) Reddy, R. P.; Lee, G. H.; Davies, H. M. L. Org. Lett. 2006, 8, 3437.
53. (b) Davies, H. M. L.; Grazini, M. V. A.; Aouad, E. Org. Lett. 2001, 3, 1475.
54. Doyle, M. P.; Hu, W.; Weathers, T. M., Jr. Chirality 2003, 15, 369.
55. Che, C-M.; Huang, J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.-M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119.
56. (a) Davies, H. M. L.; Hansen, T.; Churchill, M. R. J. Am. Chem. Soc. 2000, 122, 3063.
57. (b) Demonceau, A.; Moels, A. F.; Costa, J.-L. J. Mol. Catal. 1990, 58, 11.
58. (a) Yang, J.; Song, H.; Xiao, X.; Wang, J.; Qin, Y. Org. Lett. 2006, 8, 2187.
59. (b) Bao, Z.; Wee, A. G. H. Chem. Commun. 2008, 4837.
60. Cyclopropylindoline is known to ring-open at the C2 position; the C3-selective ring-opening is rare, see for an example: Jung, M. E.; Slowinski, F. Tetrahedron Lett. 2001, 42, 6835.