Facile regiospecific synthesis of 2,3-disubstituted indoles from isatins

Chemical Communications

Volumn 50, Issue 67, 2014, Pages 9469-9472

  Dou, Xiaowei ^a   Yao, Weijun ^a   Wen, Shan ^a   Lu, Yixin ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; GRIGNARD REAGENT; INDOLE DERIVATIVE; ISATIN DERIVATIVE; ISATIN;

ARTICLE; DRUG INDUSTRY; FACILE REGIOSPECIFIC SYNTHESIS; MEDICINAL CHEMISTRY; REDUCTION; SYNTHESIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

CHEMISTRY TECHNIQUES, SYNTHETIC; INDOLES; ISATIN; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84904985340     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc04555f     Document Type: Article

References (63)

1. M. Inman, C. J. Moody, Chem. Sci., 2013, 4, 29
2. A. J. Kochanowska-Karamyan, Chem. Rev., 2010, 110, 4489
3. T. Kawasaki, K. Higuchi, Nat. Prod. Rep., 2007, 24, 843
4. T. Kawasaki, K. Higuchi, Nat. Prod. Rep., 2005, 22, 761
5. M. Somei, F. Yamada, Nat. Prod. Rep., 2005, 22, 73
6. M. Somei, F. Yamada, Nat. Prod. Rep., 2004, 21, 278
7. R. J. Sundberg, Indoles, Academic Press, San Diego, 1996
8. M. Shiri, Chem. Rev., 2012, 112, 3508
9. S. Cacchi, G. Fabrizi, Chem. Rev., 2011, 111, PR215
10. D. F. Taber, P. K. Tirunahari, Tetrahedron, 2011, 67, 7195
11. R. Vicente, Org. Biomol. Chem., 2011, 9, 6469
12. K. Krüger, A. Tillack, M. Beller, Adv. Synth. Catal., 2008, 350, 2153
13. G. R. Humphrey, J. T. Kuethe, Chem. Rev., 2006, 106, 2875
14. S. Cacchi, G. Fabrizi, Chem. Rev., 2005, 105, 2873
15. G. Bartoli, R. Dalpozzo, M. Mardi, Chem. Soc. Rev., 2014, 43, 4728
16. D. L. Hughes, Org. Prep. Proced. Int., 1993, 25, 607
17. B. Robinson, The Fischer Indole Synthesis Wiley-Interscience, New York, 1982
18. B. Robinson, Chem. Rev., 1969, 69, 227
19. B. Robinson, Chem. Rev., 1963, 63, 373
20. M. Inman, A. Carbone, C. J. Moody, J. Org. Chem., 2012, 77, 1217
21. M. Inman, C. J. Moody, Chem. Commun., 2011, 47, 788
22. B. A. Haag, Z.-G. Zhang, J.-S. Li, P. Knochel, Angew. Chem., Int. Ed., 2010, 49, 9513
23. K. Alex, A. Tillack, N. Schwarz, M. Beller, Angew. Chem., Int. Ed., 2008, 47, 2304
24. C. Cao, Y. Shi, A. L. Odom, Org. Lett., 2002, 4, 2853
25. S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 6621
26. G. Zeni, R. C. Larock, Chem. Rev., 2006, 106, 4644
27. R. C. Larock, E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689
28. R. C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem., 1998, 63, 7652
29. D. Zhao, Z. Shi, F. Glorius, Angew. Chem., Int. Ed., 2013, 52, 12426
30. C. Wang, H. Sun, Y. Fang, Y. Huang, Angew. Chem., Int. Ed., 2013, 52, 5795
31. B. Liu, C. Song, C. Sun, S. Zhou, J. Zhu, J. Am. Chem. Soc., 2013, 135, 16625
32. C. Wang, Y. Huang, Org. Lett., 2013, 15, 5294
33. M. P. Huestis, L. Chan, D. R. Stuart, K. Fagnou, Angew. Chem., Int. Ed., 2011, 50, 1338
34. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc., 2010, 132, 18326
35. D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc., 2008, 130, 16474
36. S. P. Breazzano, Y. B. Poudel, D. L. Boger, J. Am. Chem. Soc., 2013, 135, 1600
37. Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y. Cui, N. Jiao, Angew. Chem., Int. Ed., 2009, 48, 4572
38. Z. Shi, F. Glorius, Angew. Chem., Int. Ed., 2012, 51, 9220
39. Y. Wei, I. Deb, N. Yoshikai, J. Am. Chem. Soc., 2012, 134, 9098
40. T. Nanjo, C. Tsukano, Y. Takemoto, Org. Lett., 2012, 14, 4270
41. J. J. Neumann, S. Rakshit, T. Dröge, S. Würtz, F. Glorius, Chem. Eur. J., 2011, 17, 7298
42. Y. Tan, J. F. Hartwig, J. Am. Chem. Soc., 2010, 132, 3676
43. S. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, F. Glorius, Angew. Chem., Int. Ed., 2008, 47, 7230
44. A. Gogoi, S. Guin, S. K. Rout, B. K. Patel, Org. Lett., 2013, 15, 1802
45. B. Lu, Y. Luo, L. Liu, L. Ye, Y. Wang, L. Zhang, Angew. Chem., Int. Ed., 2011, 50, 8358
46. Z.-H. Guan, Z.-Y. Yan, Z.-H. Ren, X.-Y. Liu, Y.-M. Liang, Chem. Commun., 2010, 46, 2823
47. R. Bernini, G. Fabrizi, A. Sferrazza, S. Cacchi, Angew. Chem., Int. Ed., 2009, 48, 8078
48. M. Shen, B. E. Leslie, T. G. Driver, Angew. Chem., Int. Ed., 2008, 47, 5056
49. W. Yu, Y. Du, K. Zhao, Org. Lett., 2009, 11, 2417
50. K. Alex, N. Schwarz, V. Khedkar, I. A. Sayyed, A. Tillack, D. Michalik, J. Holenz, J. L. Diaz, M. Beller, Org. Biomol. Chem., 2008, 11, 2417
51. J. M. Paolak, V. V. Khau, D. R. Hutchison, M. J. Martinelli, J. Org. Chem., 1996, 61, 9055
52. A. Arcadi, S. Cacchi, V. Carnicelli, F. Marinelli, Tetrahedron, 1994, 50, 437
53. W. Wierenga, J. Griffin, M. A. Warpehoski, Tetrahedron Lett., 1983, 24, 2437
54. S. J. Garden, R. B. da Silva, A. C. Pinto, Tetrahedron, 2002, 58, 8399
55. B. Yao, Q. Wang, J. Zhu, Angew. Chem., Int. Ed., 2012, 51, 12311
56. S. Cacchi, G. Fabrizi, A. Goggiamani, A. Perboni, A. Sferrazza, P. Staqbile, Org. Lett., 2010, 12, 3279
57. B. Z. Lu, W. Zhao, H.-X. Wei, M. Dufour, V. Farina, C. H. Senanayake, Org. Lett., 2006, 8, 3271
58. H. Tokuyama, T. Yamashita, M. T. Reding, Y. Kaburagi, T. Fukuyama, J. Am. Chem. Soc., 1999, 121, 3791
59. T. Fukuyama, X. Chen, G. Peng, J. Am. Chem. Soc., 1994, 116, 3127
60. K.-Y. Ye, L.-X. Dai, S.-L. You, Chem. Eur. J., 2014, 20, 3040
61. B. M. Trost, J. Xie, J. D. Sieber, J. Am. Chem. Soc., 2011, 133, 20611
62. R. C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem., 1998, 63, 7652
63. A. A. Haddach, A. Kelleman, M. V. Deaton-Rewolinski, Tetrahedron Lett., 2003, 43, 399