ZnI2-Catalyzed benzannulation of o-alkynylbenzaldehydes with alkenes leading to 1-acyl-2-substituted naphthalenes

European Journal of Organic Chemistry

Volumn , Issue 22, 2010, Pages 4211-4217

  Zhao, Xia ^a   Zhang, Xing Guo ^a   Tang, Ri Yuan ^a   Deng, Chen Liang ^a   Li, Jin Heng ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

Author keywords

Alkenes; Annulation; Fused ring systems; Zinc

Indexed keywords

EID: 77954977696     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000497     Document Type: Article

References (75)

1. a) A. I. Meyers, J.J. Willemsen, Tetrahedron Lett. 1996, 37, 791-792
2. b) M. Medarde, A. C. Ramos, E. Caballero, J. L. Lopez, Tetrahedron Lett. 1996, 37, 2663-2666
3. c) A. R. Katritzky, G. Zhang, L. Xie, J. Org. Chem. 1997, 62, 721-725
4. d) J. Svoboda, V. Novotna, V. Kozmik, M. Glogarova, W. Weissflog, S. Diele, G. Pelzl, J. Mater. Chem. 2003, 13, 2104-2110
5. e) R. A. Reddy, U. Baumeister, C. Keith, C. Tschierske, J. Mater. Chem. 2007, 17, 62-75
6. f) A. G. M. Barrett, F. Blaney, A. D. Campbell, D. Hamprecht, T. Meyer, A. J. P. White, D. Witty, D. J. Williams, J. Org. Chem. 2002, 67, 2735-2750
7. g) J. E. Anthony, Angew. Chem. Int. Ed. 2008, 47, 452-483
8. h) C. B. de Koning, A. Rousseau, W. A. L. van Otterlo, Tetrahedron 2003, 59, 7-36
9. i) A. R. Katritzky, J. Li, L. Xie, Tetrahedron 1999, 55, 8263
10. j) R. S. Ward, Nat. Prod. Rep. 1995, 12, 183-205
11. k) S. T. Perri, H. W. Moore, Tetrahedron Lett. 1987, 28, 4507-4510
12. l) M. Shibuya, K. Toyooka, S. Kubota, Tetrahedron Lett. 1984, 25, 1171-1174
13. m) T. F. Buckley III, H. Rapoport, J. Org. Chem. 1983, 48, 4222-4232
14. n) M. L. Bremmer, N. A. Khatri, S. M. Weinreb, J. Org. Chem 1983, 48, 3661-3666.
15. For selected reviews, see: a) R. Norman, J. M. Coxon, Principles of Organic Synthesis, 3rd ed., Chapman & Hall, New York, 1993
16. b) N. E. Shore, Chem. Rev. 1988, 88, 1081-1119
17. c) A. R. Katritzky, J. Li, L. Xie, Tetrahedron 1999, 55, 8263-8293
18. d) K. H. Dötz, P. Tomuschat, Chem. Soc. Rev. 1999, 28, 187-198
19. e) D. Astruc (Ed.), Modern Arene Chemistry, WileyVCH, Weinheim, 2002
20. f) P. Knöchel (Ed.), Handbook of Functionalized, Organometallics, Wiley-VCH, Weinheim, 2005
21. g) R. E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. Int. Ed. 2007, 46, 3802-3824
22. h) D. Mal, P. Pahari, Chem. Rev. 2007, 107, 1892-1918.
23. For special reviews, see: a) S. Saito, Y. Yamamoto, Chem. Rev. 2000, 100, 2901-2916
24. b) Y. Yamamoto, Curr. Org. Chem. 2005, 9, 503-519
25. c) S. Kotha, E. Brahmachary, K. Lahiri, Eur. J. Org. Chem. 2005, 4741-4767
26. d) B. R. Galan, T. Rovis, Angew. Chem. Int. Ed. 2009, 48, 2830-2834.
27. For selected reviews on Diels-Alder reactions, see: a) J. A. Norton, Chem. Rev. 1942, 31, 319-523
28. b) G. Brieger, J. N. Bennett, Chem. Rev. 1980, 80, 63-97
29. c) D. Craig, Chem. Soc. Rev. 1987, 16, 187-238
30. d) J. D. Winkler, Chem. Rev. 1996, 96, 167-176
31. e) K.-i. Takao, R. Munakata, K.-i. Tadano, Chem. Rev. 2005, 105, 4779-4807
32. f) P. Wessig, G. Müller, Chem. Rev. 2008, 108, 2051-2063
33. g) S. Reymond, J. Cossy, Chem. Rev. 2008, 108, 5359-5406.
34. Au: a) A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554
35. b) T. Shibata, Y. Ueno, K. Kanda, Synlett 2006, 411-414
36. c) J. Zhao, C. O. Hughes, F. D. Toste, J. Am, Chem. Soc. 2006, 128, 7436-7437
37. d) J.-J. Lian, P.-C. Chen, Y.-P. Lin, H.-C. Ting, R.-S. Liu, J. Am. Chem. Soc. 2006, 128, 11372-11373
38. e) A. S. Dudnik, T. Schwier, V. Gevorgyan, Org. Lett. 2008, 10, 1465-1468
39. f) A. S. Dudnik, T. Schwier, V. Gevorgyan, Tetrahedron 2009, 65, 1859-1870 Au or Cu:
40. g) N. Asao, K. Sato, Menggenbateer, Y. Yamamoto, J. Org. Chem, 2005, 70, 3682-3685.
41. For papers on Lewis acid catalyzed intermolecular benzannulation of alkynes with Au, see: a) J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812
42. b) N. Asao, H. Aikawa, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 7458-7459
43. c) N. Asao, T. Nogami, S. Lee, Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 10921-10925
44. d) N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am, Chem. Soc. 2002, 124, 12650-12651
45. e) D. J. Gorin, I. D. G. Watson, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 3736-3737; Ga:
46. f) G. S. Viswanathan, M. Wang, C.-J. Li, Angew. Chem, Int. Ed. 2002, 41, 2138-2141
47. 4:
48. h) G. W. Kabalka, Y. Ju, Z. Wu, J. Org. Chem. 2003, 68, 7915-7917.
49. For selected recent papers on the synthesis of naphthalenes, see: a) X. Zhang, S. Sarkar, R. C. Larock, J. Org. Chem. 2006, 71, 236-243
50. b) T. Hamura, T. Suzuki, T. Matsumoto, K. Suzuki, Angew. Chem. Int. Ed. 2006, 45, 6294-6296
51. c) L.-X. Shao, Y.-P. Zhang, M.-H. Qi, M. Shi, Org. Lett. 2007, 9, 117-120
52. d) S. Duan, D. K. Sinha-Mahapatra, J. W. Herndon, Org. Lett. 2008, 10, 1541-1544
53. e) A. C. Glass, B. B. Morris, L. N. Zakharov, S.-Y. Liu, Org. Lett. 2008, 10, 4855-4857
54. f) M. Shimizu, I. Nagao, Y. Tomioka, T. Hiyama, Angew. Chem, Int. Ed. 2008, 47, 8096-8099
55. g) T. Dohi, M. Ito, K. Morimoto, M. Iwata, Y Kita, Angew. Chem. Int. Ed. 2008, 47, 1301-1304
56. h) Z. Chen, W. Shou, Y. Wang, Synthesis 2009, 1075-1080.
57. a) N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem, Soc. 2002, 124, 12650-12651; a review:
58. b) Y. Yamamoto, I. D. Gridnev, N. T. Patil, T. Jin, Chem. Commun. 2009, 5075-5087.
59. N. Asao, T. Kasahara, Y. Yamamoto, Angew. Chem. Int. Ed. 2003, 42, 3504-3506.
60. G. Dyker, D. Hildebrandt, J. Liu, K. Merz, Angew. Chem. Int. Ed. 2003, 42, 4399-4402.
61. For a DFT study of the mechanism, see: B. F. Straub, Chem. Commun. 2004, 1726-1728.
62. For Lewis acid catalyzed nucleophilic cyclization of 2- alkynylbenzaldehydes for the synthesis of 1H-isochromenes, see: a) N. T. Patil, Y. Yamamoto, J. Org. Chem, 2004, 69, 5139-5142
63. b) X. Yu, Q. Ding, W. Wang, X Wu, Tetrahedron Lett. 2008, 49, 4390-4393
64. c) F. Wang, Z. Miao, R. Chen, Org Biomol. Chem. 2009, 7, 2848-2850
65. d) R.-Y. Tang, J.-H. Li, Chem, Eur. J. 2010, 16, 4733-4738.
66. For electrophilic cyclization, see: a) D. Yue, N. Delia Ca, R. C. Larock, Org. Lett. 2004, 6, 1581-1584
67. b) D. Yue, N. Delia Ca, R. C. Larock, J. Org. Chem. 2006, 71, 3381-3388
68. c) J. Barluenga, H. Vázquez-Villa, I. Merino, A. Ballesteros, J. M. González, Chem. Eur. J. 2006, 12, 5790-5805
69. d) J. Barluenga, H. Vazquez-Villa, A. Ballesteros, I M. Gonzalez, Org. Lett. 2003, 5, 4121-4123.
70. Z.-L. Hu, W.-J. Qian, S. Wang, S. Wang, Z.-J. Yao, Org. Lett. 2009, 11, 4676-4679.
71. C.-L. Deng, R.-J. Song, Y.-L. Liu, J.-H. Li, Adv. Synth, Catal. 2009, 351, 3096-3100.
72. a) A. Kong, X. Hang, X. Lu, Org. Lett. 2006, 8, 1339-1342
73. b) X. Hang, X. Lu, Org. Lett. 2009, 11, 2381-2384.
74. CCDC-775610 (for 8) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
75. J.-J. Lian, R.-S. Liu, Chem, Commun. 2007, 1337-1339.