Unexpected hydrobromic acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals

Chemistry - A European Journal

Volumn 16, Issue 45, 2010, Pages 13450-13457

  Yuan, Hongjuan ^a   Wang, Mang ^a   Liu, Yingjie ^a   Wang, Lili ^a   Liu, Jun ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

C C coupling; C H activation; hydrobromic acid; oxygen heterocycles; reaction mechanisms

Indexed keywords

C-C COUPLING; C-H ACTIVATION; HYDROBROMIC ACID; OXYGEN HETEROCYCLES; REACTION MECHANISM;

ACTIVATION ANALYSIS; CARBONYLATION; CATALYSIS; CATALYSTS; INORGANIC ACIDS; OLEFINS; ORGANIC COMPOUNDS; OXYGEN; SULFUR; SYNTHESIS (CHEMICAL);

REACTION INTERMEDIATES;

EID: 78649824032     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002107     Document Type: Article

References (64)

1. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529
2. R. J. Phipps, M. J. Gaunt, Science 2009, 323, 1593
3. J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, Jr., M. R. Smith a III, Science 2002, 295, 305
4. K. Godula, D. Sames, Science 2006, 312, 67
5. C.-J. Li, Acc. Chem. Res. 2009, 42, 335.
6. 2-H activation, see
7. T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820
8. Angew. Chem. Int. Ed. Engl. 1997, 36, 1740
9. K. Tsuchikama, Y. Kuwata, Y.-k. Tahara, Y. Yoshinami, T. Shibata, Org. Lett. 2007, 9, 3097
10. K. Tanaka, Y. Otake, A. Wada, K. Noguchi, M. Hirano, Org. Lett. 2007, 9, 2203.
11. 2-H activation, see
12. D. A. Colby, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2006, 128, 5604
13. X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790
14. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404
15. I. Özdemir, S. Demir, B. Cetinkaya, C. Gourlaouen, F. Maseras, C. Bruneau, P. H. Dixneuf, J. Am. Chem. Soc. 2008, 130, 1156
16. M. Kim, J. Kwak, S. Chang, Angew. Chem. 2009, 121, 9097
17. Angew. Chem. Int. Ed. 2009, 48, 8935.
18. R. K. Dieter, Tetrahedron 1986, 42, 3029
19. H. Junjappa, H. Ila, C. V. Asokan, Tetrahedron 1990, 46, 5423.
20. X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, B. Li, J. Am. Chem. Soc. 2005, 127, 4578
21. D. Dong, X. Bi, Q. Liu, F. Cong, Chem. Commun. 2005, 3580
22. J. Tan, X. Xu, L. Zhang, Y. Li, Q. Liu, Angew. Chem. 2009, 121, 2912
23. Angew. Chem. Int. Ed. 2009, 48, 2868
24. M. Wang, F. Han, H. Yuan, Q. Liu, Chem. Commun. 2010, 46, 2247
25. Y. Li, X. Xu, J. Tan, P. Liao, J. Zhang, Q. Liu, Org. Lett. 2010, 12, 244
26. H. Yu, Z. Yu, Angew. Chem. 2009, 121, 2973
27. Angew. Chem. Int. Ed. 2009, 48, 2929
28. P. P. Singh, A. K. Yadav, H. Ila, H. Junjappa, J. Org. Chem. 2009, 74, 5496
29. H. S. P. Rao, K. Vasantham, J. Org. Chem. 2009, 74, 6847
30. M. Hagimori, S. Matsui, N. Mizuyama, K. Yokota, J. Nagaoka, Y. Tominaga, Eur. J. Org. Chem. 2009, 5847
31. X. Gao, C. Di, Y. Hu, X. Yang, H. Fan, F. Zhang, Y. Liu, H. Li, D. Zhu, J. Am. Chem. Soc. 2010, 132, 3697
32. S. Yoshida, H. Yorimitsu, K. Oshima, Org. Lett. 2009, 11, 2185
33. S. Yoshida, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 5573.
34. T. Minami, T. Okauchi, H. Matsuki, M. Nakamura, J. Ichikawa, M. Ishida, J. Org. Chem. 1996, 61, 8132
35. R. Kouno, T. Okauchi, M. Nakamura, J. Ichikawa, T. Minami, J. Org. Chem. 1998, 63, 6239.
36. T. Okauchi, T. Tanaka, T. Minami, J. Org. Chem. 2001, 66, 3924
37. S. Yahiro, K. Shibata, T. Saito, T. Okauchi, T. Minami, J. Org. Chem. 2003, 68, 4947.
38. Y. Yin, M. Wang, Q. Liu, J. Hu, S. Sun, J. Kang, Tetrahedron Lett. 2005, 46, 4399
39. S. Sun, Q. Zhang, Q. Liu, J. Kang, Y. Yin, D. Li, D. Dong, Tetrahedron Lett. 2005, 46, 6271
40. Q. Zhang, Y. Liu, M. Wang, Q. Liu, J. Hu, Y. Yin, Synthesis 2006, 3009
41. Z. Fu, M. Wang, Y. Ma, Q. Liu, J. Liu, J. Org. Chem. 2008, 73, 7625
42. Y. Ma, M. Wang, D. Li, B. Bekturhun, J. Liu, Q. Liu, J. Org. Chem. 2009, 74, 3116.
43. H.-J. Yuan, M. Wang, Y.-J. Liu, Q. Liu, Adv. Synth. Catal. 2009, 351, 112
44. Y. Liu, M. Wang, H. Yuan, Q. Liu, Adv. Synth. Catal. 2010, 352, 884
45. D. Liang, M. Wang, B. Bekturhun, B. Xiong, Q. Liu, Adv. Synth. Catal. 2010, 352, 1593.
46. R. O. Kennedy, R. D. Tharnes, Coumarins: Biology Application and Mode of Action, Wiley, New York, 1997
47. R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins: Occurrence Chemistry and Biochemistry, Wiley, New York, 1982.
48. W. B. Jensen, Chem. Rev. 1978, 78, 1
49. G. A. Olah, S. Kobayashi, M. Tashiro, J. Am. Chem. Soc. 1972, 94, 7448.
50. D. Dong, Y. Ouyang, H. Yu, Q. Liu, J. Liu, M. Wang, J. Zhu, J. Org. Chem. 2005, 70, 4535
51. Q. Liu, G. Che, H. Yu, Y. Liu, J. Zhang, Q. Zhang, D. Dong, J. Org. Chem. 2003, 68, 9148.
52. 1Ha NMR spectra in the Supporting Information for this experiment). The stepwise decrease in the peak area at δ=5.43a ppm indicates that the α-hydrogen of 1a is gradually deuterated under the acidic conditions. This experiment thus provides evidence for the transformation of 1 into intermediate A as described in Schemea 5.
53. M. Gonsior, I. Krossing, Chem. Eur. J. 2004, 10, 5730.
54. A. Fürstner, M. Alcarazo, R. Goddard, C. W. Lehmann, Angew. Chem. 2008, 120, 3254
55. Angew. Chem. Int. Ed. 2008, 47, 3210
56. O. Kaufhold, F. E. Hahn, Angew. Chem. 2008, 120, 4122
57. Angew. Chem. Int. Ed. 2008, 47, 4057
58. V. Lavallo, C. A. Dyker, B. Donnadieu, G. Bertrand, Angew. Chem. 2009, 121, 1568
59. Angew. Chem. Int. Ed. 2009, 48, 1540.
60. For the formation and reaction of nonclassical carbonium ylide, see
61. K. Vyakaranam, S. Körbe, H. Divišová, J. Michl, J. Am. Chem. Soc. 2004, 126, 15795
62. K. Vyakaranam, Z. Havlas, J. Michl, J. Am. Chem. Soc. 2007, 129, 4172.
63. O. I. Kolodiazhnyi, Phosphorus Ylides: Chemistry and Application in Organic Synthesis, Wiley-VCH, Weinheim, 1999
64. Nitrogen Oxygen and Sulfur Ylide Chemistry (Ed.:, S. J. Clark,), Oxford University Press, Oxford, 2002.