Pd-catalyzed addition of boronic acids to vinylogous imines: A convenient approach to 3-sec-alkyl substituted indoles

Tetrahedron Letters

Volumn 53, Issue 30, 2012, Pages 3873-3875

  Cao, Liang Liang ^a   Li, Xu Ni ^a   Meng, Fan Yan ^a   Jiang, Guo Fang ^a  

^a HUNAN UNIVERSITY   (China)

Author keywords

Boronic acids; Conjugate addition; Palladium; Sulfonylindoles; Vinylogous imines

Indexed keywords

ARYLBORONIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; IMINE; INDOLE DERIVATIVE; PALLADIUM; SULFONYLINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE;

EID: 84862570668     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.056     Document Type: Article

References (78)

1. J. Christoffers, G. Koripelly, A. Rosiak, and M. Rössle Synthesis 2007 1279
2. C. Hawner, and A. Alexakis Chem. Commun. 46 2010 7295
3. For recent reviews, see: T. Hayashi, and K. Yamasaki Chem. Rev. 103 2003 2829
4. K. Fagnou, and M. Lautens Chem. Rev. 103 2003 169
5. F. Glorius Angew. Chem., Int. Ed. 43 2004 3364
6. A. Gutnov Eur. J. Org. Chem. 2008 4547
7. N. Miyaura Synlett 2009 2039
8. For recent literatures on Rh-catalyzed addition reaction see: Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, and N. Miyaura J. Am. Chem. Soc. 120 1998 5579
9. M. Kuriyama, K. Nagai, K. Yamada, Y. Miwa, T. Taga, and K. Tomioka J. Am. Chem. Soc. 124 2002 8932
10. T. Hayashi, K. Ueyama, N. Tokunaga, and K. Yoshida J. Am. Chem. Soc. 125 2003 11508
11. Y.D. Ma, C. Song, C.Q. Ma, Z.J. Sun, Q. Chai, and M.B. Andrus Angew. Chem., Int. Ed. 42 2003 5871
12. R. Shintani, W.L. Duan, T. Nagano, A. Okada, and T. Hayashi Angew. Chem., Int. Ed. 44 2005 4611
13. Z.-Q. Wang, C.-G. Feng, M.-H. Xu, and G.-Q. Lin J. Am. Chem. Soc. 129 2007 5336
14. C.-G. Feng, Z.-Q. Wang, P. Tian, M.-H. Xu, and G.-Q. Lin Chem. Asian J. 3 2008 1511
15. C.-G. Feng, Z.-Q. Wang, C. Shao, M.-H. Xu, and G.-Q. Lin Org. Lett. 10 2008 4101
16. X. Hu, M. Zhuang, Z. Cao, and H. Du Org. Lett. 11 2009 4744
17. Q.-A. Chen, X. Dong, M.-W. Chen, D.-S. Wang, Y.-G. Zhou, and Y.-X. Li Org. Lett. 12 2010 1928
18. K. Ueura, T. Satoh, and M. Miura Org. Lett. 7 2005 2229
19. S. Lin, and X. Lu J. Org. Chem. 72 2007 9757
20. Select examples, see: T. Nishikata, Y. Yamamoto, and N. Miyaura Angew. Chem., Int. Ed. 42 2003 2768
21. T. Nishikata, Y. Yamamoto, and N. Miyaura Organometallics 23 2004 4317
22. X. Lu, and S. Lin J. Org. Chem. 70 2005 9651
23. T. Yamamoto, T. Ohta, and Y. Ito Org. Lett. 7 2005 4153
24. B. Zhao, and X. Lu Org. Lett. 8 2006 5987
25. G. Liu, and X. Lu J. Am. Chem. Soc. 128 2006 16504
26. S. Lin, and X. Lu Tetrahedron Lett. 47 2006 7167
27. K. Suzuki, T. Arao, S. Ishii, Y. Maeda, K. Kondo, and T. Aoyama Tetrahedron Lett. 47 2006 5789
28. P. He, Y. Lu, C.-G. Dong, and Q.-S. Hu Org. Lett. 9 2007 343
29. Z. Ye, P. Qian, G. Lv, F. Luo, and J. Cheng J. Org. Chem. 75 2010 6043
30. S. Lin, and X. Lu Org. Lett. 12 2010 2536
31. T.-P. Liu, Y.-X. Liao, C.-H. Xing, and Q.-S. Hu Org. Lett. 13 2011 2452
32. K. Kikushima, J.C. Holder, M. Gatti, and B. Stoltz J. Am. Chem. Soc. 133 2011 6902
33. S. Shirakawa, and S. Kobayashi Org. Lett. 8 2006 4939
34. B.B. Semenov, K.A. Novikov, K.A. Lysenko, and V.V. Kachala Tetrahedron Lett. 47 2006 3479
35. A. Palmieri, M. Petrini, and R.R. Shaikh Org. Biomol. Chem. 8 2010 1259
36. Q.-X. Guo, Y.-G. Peng, J.-W. Zhang, L. Song, Z. Feng, and L.-Z. Gong Org. Lett. 11 2009 4620
37. L. Marsili, A. Palmieri, and M. Petrini Org. Biomol. Chem. 8 2010 706
38. D.-S. Wang, J. Tang, Y.-G. Zhou, M.-W. Chen, Y. Duan, and G.-F. Jiang Chem. Sci. 2 2011 803
39. Y. Duan, M.-W. Chen, Z.-S. Ye, D.-S. Wang, Q.-A. Chen, and Y.-G. Zhou Chem. Eur. J. 17 2011 7193
40. B.B. Semenov, and V.G. Granik Pharm. Chem. J. 38 2004 287
41. B. Semenov, Y. Smushkevich, I. Levina, L. Kurkovskaya, K. Lysenko, and V. Kachala Chem. Heterocycl. Compd. 41 2005 730
42. G. De La Herrán, A. Segura, and A.G. Csákÿ Org. Lett. 9 2007 961
43. J.-I. Matsuo, Y. Tanaki, and H. Ishibashi Tetrahedron 64 2008 5262
44. R. Ballini, A. Palmieri, M. Petrini, and E. Torregiani Org. Lett. 8 2006 4093
45. A. Palmieri, and M. Petrini J. Org. Chem. 72 2007 1863
46. R. Ballini, A. Palmieri, M. Petrini, and R.R. Shaikh Adv. Synth. Catal. 350 2008 129
47. R.R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, and P. Melchiorre Angew. Chem., Int. Ed. 47 2008 8707
48. Y. Li, F.-Q. Shi, Q.-L. He, and S.-L. You Org. Lett. 11 2009 3182
49. M.C. Dobish, and J.N. Johnston Org. Lett. 12 2010 5744
50. L. Jing, J. Wei, L. Zhou, Z. Huang, Z. Li, D. Wu, H. Xiang, and X. Zhou Chem. Eur. J. 16 2010 10955
51. R. Ballini, S. Gabrielli, A. Palmieri, and M. Petrini Adv. Synth. Catal. 352 2010 2459
52. B.-H. Zheng, C.-H. Ding, X.-L. Hou, and L.-X. Dai Org. Lett. 12 2010 1688
53. R. Dubey, and B. Olenyuk Tetrahedron Lett. 51 2010 609
54. L.-L. Cao, Z.-S. Ye, G.-F. Jiang, and Y.-G. Zhou Adv. Synth. Catal. 353 2011 3352
55. J. Bosch, and M.-L. Bennasar Synlett 1995 587
56. D.J. Faulkner Nat. Prod. Rep. 19 2002 1
57. S. Agarwal, S. Caemmerer, S. Filali, W. Froehner, J. Knoell, M.P. Krahl, K.R. Reddy, and H.-J. Knoelker Curr. Org. Chem. 9 2005 1601
58. S.E. O'Connor, and J.J. Maresh Nat. Prod. Rep. 23 2006 532
59. For recent some reviews on synthesis of indoles and substituted indoles, see: S. Agarwal, S. Cammerer, S. Filali, W. Frohner, J. Knoll, M.P. Krahl, K.R. Reddy, and H.J. Knolker Curr. Org. Chem. 9 2005 160
60. S. Cacchi, and G. Fabrizi Chem. Rev. 105 2005 2873
61. G.R. Humphrey, and J.T. Kuethe Chem. Rev. 106 2006 2875
62. J. Hajicek Collect. Czech. Chem. Commun. 72 2007 821
63. M.A. Metwally, S. Shaaban, B.F. Abdel-Wahab, and G.A. El-Hiti Curr. Org. Chem. 13 2009 1475
64. J. Barluenga, F. Rodriguez, and F.J. Fananas Chem. Asian J. 4 2009 1036
65. M. Bandini, and A. Eichholzer Angew. Chem., Int. Ed. 48 2009 9608
66. C. Gil, and S.J. Brase Comb. Chem. 11 2009 175
67. G. Bartoli, G. Bencivenni, and R. Dalpozzo Chem. Soc. Rev. 39 2010 4449
68. Selected examples of synthesis of indoles and substituted indoles, see: Q.-L. He, F.-L. Sun, X.-J. Zeng, and S.-L. You Synlett 2009 1111
69. F.-L. Sun, M. Zeng, Q. Gu, and S.-L. You Chem. Eur. J. 15 2009 8709
70. F.-L. Sun, X.-J. Zeng, Q. Gu, Q.-L. He, and S.-L. You Eur. J. Org. Chem. 2010 47
71. A. Arcadi, R. Cianci, G. Ferrara, and F. Marinelli Tetrahedron 66 2010 2378
72. A. Boyer, N. Isono, S. Lackner, and M. Lautens Tetrahedron 66 2010 6468
73. S. Cacchi, G. Fabrizi, A. Goggiamani, A. Perboni, A. Sferrazza, and P. Stabile Org. Lett. 12 2010 3279
74. S. Chiba, L. Zhang, S. Sanjaya, and G.Y. Ang Tetrahedron 66 2010 5692
75. S. Jana, M.D. Clements, B.K. Sharp, and N. Zheng Org. Lett. 12 2010 3736
76. Y. Monguchi, S. Mori, S. Aoyagi, A. Tsutsui, T. Maegawa, and H. Sajiki Org. Biomol. Chem. 8 2010 3338
77. C.H. Oh, S. Karmakar, H. Park, Y. Ahn, and J.W.J. Kim Am. Chem. Soc. 132 2010 1792
78. L.-L. Cao, D.-S. Wang, G.-F. Jiang, and Y.-G. Zhou Tetrahedron Lett. 52 2011 2837