Direct functionalization of indoles: Copper-catalyzed malonyl carbenoid insertions

Organic Letters

Volumn 12, Issue 21, 2010, Pages 4956-4959

  Johansen, Michael B ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; COPPER; DRUG DERIVATIVE; INDOLE DERIVATIVE; METHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; COPPER; INDOLES; METHANE; MOLECULAR STRUCTURE;

EID: 78049521755     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1020948     Document Type: Article

References (52)

1. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
2. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
3. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
4. Sundberg, R. J., Indoles; Academic: New York, 1996.
5. For recent examples see
6. Yan, G.; Kuang, C.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 1052
7. Yang, L.; Zhao, L.; Li, C.-J. J. Chem. Soc., Chem. Commun. 2010, 46, 4181
8. Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2096
9. Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346
10. Luzung, M. R.; Lewis, C. A.; Baran, P. S. Angew. Chem., Int. Ed. 2009, 48, 7025
11. Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172
12. Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172
13. Stuart, D. R.; Villemure, E.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 12072
14. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050
15. Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 117, 3185
16. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578 For recent reviews see: Joucla, L.; Djakovitch, L. Adv. Synth. Catal. 2009, 351, 673
17. Bellina, F.; Rossi, R. Tetrahedron 2009, 65, 10269
18. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
19. For representative examples see
20. Jackson, R. W.; Manske, R. H. Can. J. Res. 1935, 13B, 170
21. Welstead, W. J. J.; Stauffer, H. F.; Sancilio, L. F. J. Med. Chem. 1974, 17, 544
22. Wenkert, E.; Alonso, M. E.; Gottlieb, H. E.; Sanchez, E. L.; Pellicciari, R.; Cogolli, P. J. Org. Chem. 1977, 42, 3945
23. Keller, H.; Langer, E.; Lehner, H. Monatsh. Chem. 1977, 108, 123
24. Chan, W.-W.; Yeung, S.-H.; Zhou, Z.; Chan, A. S. C.; Yu, W.-Y. Org. Lett. 2010, 12, 604
25. Lian, Y.; Davies, H. M. L. Org. Lett. 2010, 12, 924
26. Lian, Y.; Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 440
27. Antos, J. M.; McFarland, J. M.; Iavarone, A. T.; Francis, M. B. J. Am. Chem. Soc. 2009, 131, 6301
28. Rosenberg, M. L.; Aasheim, J. H. F.; Trebbin, M.; Uggerud, E.; Hansen, T. Tetrahedron Lett. 2009, 50, 6506
29. Zhang, X.-J.; Liu, S.-P.; Yan, M. Chin. J. Chem. 2008, 26, 716
30. Zhang, B.; Wee, A. G. H. J. Chem. Soc., Chem. Commun. 2008, 39, 4837
31. Muthusamy, S.; Gnanaprakasam, B. Tetrahedron Lett. 2009, 49, 475
32. Song, H.; Yang, J.; Chen, W.; Qin, Y. Org. Lett. 2006, 8, 6011
33. Cuevas-Yañez, E.; Muchowski, J. M.; Cruz-Almanza, R. Tetrahedron 2004, 60, 1505
34. Gnad, F.; Poleschak, M.; Reiser, O. Tetrahedron Lett. 2004, 45, 4277
35. Yadav, J. S.; Reddy, B. V. S.; Satheesh, G. Tetrahedron Lett. 2003, 44, 8331
36. Muthusamy, S.; Gunanathan, C.; Babu, S. A.; Suresh, E.; Dastidar, P. J. Chem. Soc., Chem. Commun. 2002, 824
37. Jung, M. E.; Slowinski, F. Tetrahedron Lett. 2001, 42, 6835
38. Salim, M.; Capretta, A. Tetrahedron 2000, 56, 8063
39. Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1997, 119, 9641
40. Babu, S. D.; Hrytsak, M. D.; Durst, T. Can. J. Chem. 1989, 67, 1071
41. Zhang, M.; Huang, X.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2009, 131, 6013
42. Shen, L.; Zhang, M.; Qin, Y. Angew. Chem., Int. Ed. 2008, 47, 3618
43. He, B.; Song, H.; Qin, Y. J. Org. Chem. 2009, 74, 298
44. Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794
45. Gibe, R.; Kerr, M. A. J. Org. Chem. 2002, 67, 6247
46. Martin, C. L.; Overman, L. E.; Rhode, J. M. J. Am. Chem. Soc. 2010, 132, 4894
47. Kaburagi, Y.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2004, 126, 10246
48. For example see
49. Lim, K.-H.; Kam, T.-S. Org. Lett. 2006, 8, 1733
50. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; John Wiley & Sons: New York, 1998.
51. 1H NMR.
52. 85% recovered 5q based on expected return, given 55% 7q isolated.