An indium(III)-catalyzed synthesis of 4,4-dichloro-1-aryl-N-alkyl-1-yn-3- amines via an intermolecular C(sp2)-C(sp) bond formation

Advanced Synthesis and Catalysis

Volumn 354, Issue 18, 2012, Pages 3461-3467

  Malakar, Chandi C ^a   Maes, Bert U W ^a   Tehrani, Kourosch Abbaspour ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

chloro imines; A2 coupling; C H activation; indium(III) catalysis; propargylic amines

Indexed keywords

EID: 84871033706     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200680     Document Type: Article

References (68)

1. M. A. Huffman, N. Yasuda, A. E. DeCamp, E. J. J. Grabowski, J. Org. Chem. 1995, 60, 1590
2. M. Miura, M. Enna, K. Okuro, M. Nomura, J. Org. Chem. 1995, 60, 4999
3. A. Jenmalm, W. Berts, Y. L. Li, K. Luthman, I. Csoregh, U. Hacksell, J. Org. Chem. 1994, 59, 1139.
4. For reviews see
5. G. Dyker, Angew. Chem. 1999, 111, 1808
6. Angew. Chem. Int. Ed. 1999, 38, 1698
7. T. Naota, H. Takaya, S. I. Murahashi, Chem. Rev. 1998, 98, 2599. For selected examples see
8. J. J. Fleming, J. Du Bois, J. Am. Chem. Soc. 2006, 128, 3926
9. B. Jiang, M. Xu, Angew. Chem. 2004, 116, 2597
10. Angew. Chem. Int. Ed. 2004, 43, 2543
11. T. Yoon, M. D. Shair, S. J. Danishefsky, G. K. Shulte, J. Org. Chem. 1994, 59, 3752.
12. M. Dhooghe, W. Van Brabandt, N. De Kimpe, J. Org. Chem. 2004, 69, 2709, and references cited therein
13. J. L. Wright, T. F. Gregory, S. P. Kesten, P. A. Boxer, K. A. Serpa, L. T. Meltzer, L. D. Wise, S. A. Espitia, C. S. Konkoy, E. R. Whittemore, R. M. Woodward, J. Med. Chem. 2000, 43, 3408.
14. M. Naoi, W. Maruyama, M. B. H. Youdim, P. Yu, A. A. Boulton, Inflammopharmacology 2003, 11, 175.
15. P. H. Yu, B. A. Davis, A. A. Boulton, J. Med. Chem. 1992, 35, 3705.
16. For selected examples see
17. A. Hoepping, K. M. Johnson George, J. Flippen-Anderson, A. P. Kozikowski, J. Med. Chem. 2000, 43, 2064
18. N. Miyachi, F. Kanda, M. Shibasaki, J. Org. Chem. 1989, 54, 3511
19. M. Shibasaki, Y. Ishida, G. Iwasaki, T. Iimori, J. Org. Chem. 1987, 52, 3488.
20. C. Swithenbank, P. J. McNulty, K. L. Viste, J. Agric. Food Chem. 1971, 19, 417.
21. For selected examples see
22. H. Eshghi, G. H. Zohuri, S. Damavandia, Eur. J. Chem. 2011, 2, 100
23. P. de Armas, D. Tejedor, F. García-Tellado, Angew. Chem. 2010, 122, 1029
24. Angew. Chem. Int. Ed. 2010, 49, 1013
25. J. Mao, P. Zhang, Tetrahedron: Asymmetry 2009, 20, 566
26. D. A. Black, R. E. Beveridge, B. A. Arndtsen, J. Org. Chem. 2008, 73, 1906
27. C. Wei, J. T. Mague, C.-J. Li, Proc. Natl. Acad. Sci. USA 2004, 101, 5749
28. B. Jiang, Y.-G. Si, Tetrahedron Lett. 2003, 44, 6767.
29. For selected examples see
30. [l8-27] cited therein
31. Y. Zhang, P. Li, M. Wang, L. Wang, J. Org. Chem. 2009, 74, 4364
32. B. M. Trost, A. H. Weissb, Adv. Synth. Catal. 2009, 351, 963
33. D. Tejedor, S. López-Tosco, F. Cruz-Acosta, G. Méndez-Abt, F. García-Tellado, Angew. Chem. 2009, 121, 2124
34. Angew. Chem. Int. Ed. 2009, 48, 2090
35. M. Irmaka, M. M. K. Boysena, Adv. Synth. Catal. 2008, 350, 403
36. Z. Shao, J. Wang, K. Ding, A. S. C. Chan, Adv. Synth. Catal. 2007, 349, 2375
37. L. Zani, T. Eichhorn, C. Bolm, Chem. Eur. J. 2007, 13, 2587
38. T. R. Wu, J. M. Chong, Org. Lett. 2006, 8, 15
39. N. Gommermann, P. Knochel, Chem. Eur. J. 2006, 12, 4380
40. T. F. Knöpfel, P. Aschwanden, T. Ichikawa, T. Watanabe, E. M. Carreira, Angew. Chem. 2004, 116, 6097
41. Angew. Chem. Int. Ed. 2004, 43, 5971
42. N. Gommermann, C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2003, 115, 5941
43. Angew. Chem. Int. Ed. 2003, 42, 5763
44. J. F. Traverse, A. H. Hoveyda, M. L. Snapper, Org. Lett. 2003, 5, 3273
45. C. Koradin, K. Polborn, P. Knochel, Angew. Chem. 2002, 114, 2651
46. Angew. Chem. Int. Ed. 2002, 41, 2535
47. B. Jiang, Y.-G. Si, Tetrahedron Lett. 2003, 44, 6767
48. C. Wei, C.-J. Li, J. Am. Chem. Soc. 2002, 124, 5638; for recent reviews see
49. S. Kobayashi, Y. Mori, J. S. Fossey, M. M. Salter, Chem. Rev. 2011, 111, 2626
50. K.-I. Yamada, K. Tomioka, Chem. Rev. 2008, 108, 2874
51. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2004, 4095.
52. S. Stas, K. Abbaspour Tehrani, Tetrahedron 2007, 63, 8921
53. A. S. Konev, S. Stas, M. S. Novikov, A. F. Khlebnikov, K. Abbaspour Tehrani, Tetrahedron 2008, 64, 117
54. S. Stas, K. Abbaspour Tehrani, G. Laus, Tetrahedron 2008, 64, 3457
55. K. Abbaspour Tehrani, S. Stas, B. Lucas, N. De Kimpe, Tetrahedron 2009, 65, 1957.
56. R. Takita, Y. Fukuta, R. Tsuji, T. Ohshima, M. Shibasaki, Org. Lett. 2005, 7, 1363
57. R. Takita, K. Yakura, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 13760.
58. For a recent review on the use of indium salts in organic synthesis, see:, J. Augé, N. Lubin-Germain, J. Uziel, Synthesis 2007, 1739; for an example on functional group tolerance see
59. Y.-H. Chen, P. Knochel, Angew. Chem. 2008, 120, 7760
60. Angew. Chem. Int. Ed. 2008, 47, 7648.
61. For reviews on In(III) catalysis see
62. J.-F. Zhao, H.-Y. Tsui, P.-J. Wu, J. Lu, T.-P. Loh, J. Am. Chem. Soc. 2008, 130, 16492
63. Y. Itoh, H. Tsuji, K.-I. Yamagata, K. Endo, I. Tanaka, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 17161
64. K. K. Chauhan, C. G. Frost, J. Chem. Soc. Perkin Trans. 1 2000, 3015.
65. Azomethine-azomethine isomerizations mostly occur under strongly basic conditions
66. N. De Kimpe, D. De Smaele, A. Hofkens, Y. Dejaegher, B. Kesteleyn, Tetrahedron 1997, 53, 10803
67. T. Ono, V. P. Kukhar, V. A. Soloshonok, J. Org. Chem. 1996, 61, 6563.
68. [10d]).