Four iodine-mediated electrophilic cyclizations of rigid parallel triple bonds mapped from 1,8-dialkynylnaphthalenes

Chemistry - A European Journal

Volumn 17, Issue 29, 2011, Pages 8105-8114

  Chen, Xiaopeng ^a   Lu, Ping ^a   Wang, Yanguang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

fluorescence; heterocyces; iodocyclization; parallel diynes; tandem reactions

Indexed keywords

ACENAPHTHYLENE; CYCLIZATIONS; EMISSION EFFICIENCIES; EMITTED LIGHT; FLUORANTHENE; HETEROCYCES; IODOCYCLIZATION; OXIDATIVE COUPLINGS; PARALLEL DIYNES; PERYLENE DERIVATIVES; SINGLE-STEP; TANDEM REACTION; THEORETICAL CALCULATIONS; TRIPLE BONDS;

CYCLIZATION; DICHLOROMETHANE; IODINE; NAPHTHALENE;

INDUSTRIAL CHEMICALS;

EID: 79959971605     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100858     Document Type: Article

References (85)

1. For reviews of iodocyclization, see: a) H. Togo, S. Iida, Synlett 2006, 2159
2. R. C. Larock, Acetylene Chem. 2005, 51
3. A. N. French, S. Bissmire, T. Wirth, Chem. Soc. Rev. 2004, 33, 354.
4. For selected examples, see a) H. C. Ouyang, R. Y. Tang, P. Zhong, X. G. Zhang, J.-H. Li, J. Org. Chem. 2011, 76, 223
5. T. Okitsu, K. Sato, A. Wada, Org. Lett. 2010, 12, 3506
6. R. Halim, P. J. Scammells, B. L. Flynn, Org. Lett. 2008, 10, 1967
7. K. O. Hessian, B. L. Flynn, Org. Lett. 2006, 8, 243
8. D. Yue, R. C. Larock, Org. Lett. 2004, 6, 1037
9. J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2003, 115, 2508
10. Angew. Chem. Int. Ed. 2003, 42, 2406.
11. For selected examples, see: a)A. K. Verma, T. Aggarwal, V. Rustagi, R. C. Larock, Chem. Commun. 2010, 46, 4064
12. K. G. Ji, H. T. Zhu, F. Yang, A. Shaukat, X. F. Xia, Y. F. Yang, X. Y. Liu, Y. M. Liang, J. Org. Chem. 2010, 75, 5670
13. Z. W. Just, R. C. Larock, J. Org. Chem. 2008, 73, 2662
14. S. Arimitsu, J. M. Jacobsen, G. B. Hammond, J. Org. Chem. 2008, 73, 2886
15. J. Barluenga, H. Vázquez-Villa, I. Merino, A. Ballesteros, J. M. González, Chem. Eur. J. 2006, 12, 5790.
16. For selected examples, see: a)C. H. Cho, D. -I Jung, R. C. Larock, Tetrahedron Lett. 2010, 51, 6485
17. C. T. Bui, B. L. Flynn, J. Comb. Chem. 2006, 8, 163
18. K. O. Hessian, B. L. Flynn, Org. Lett. 2003, 5, 4377
19. B. L. Flynn, P. Verdier-Pinard, E. Hamel, Org. Lett. 2001, 3, 651.
20. For selected examples, see: a)D. R. Garud, M. Koketsu, Org. Lett. 2008, 10, 3319
21. D. Alves, C. Luchese, C. W. Nogueira, G. Zeni, J. Org. Chem. 2007, 72, 6726
22. T. Kesharwani, S. A. Worlikar, R. C. Larock, J. Org. Chem. 2006, 71, 2307.
23. For selected examples, see: a)B. Crone, S. F. Kirsch, K. D. Umland, Angew. Chem. 2010, 122, 4765
24. Angew. Chem. Int. Ed. 2010, 49, 4661
25. X. Zhang, T. Yao, M. A. Campo, R. C. Larock, Tetrahedron 2010, 66, 1177
26. S. A. Worlikar, T. Kesharwani, T. Yao, R. C. Larock, J. Org. Chem. 2007, 72, 1347
27. J. Barluenga, M. Trincado, E. Rubio, J. M. González, Angew. Chem. 2006, 118, 3212
28. Angew. Chem. Int. Ed. 2006, 45, 3140
29. X. Zhang, S. Sarkar, R. C. Larock, J. Org. Chem. 2006, 71, 236
30. J. Barluenga, M. Trincado, M. Marco-Arias, A. Ballesteros, E. Rubio, J. M. González, Chem. Commun. 2005, 2008
31. T. Yao, M. A. Campo, R. C. Larock, Org. Lett. 2004, 6, 2677.
32. J. M. W. Chan, J. R. Tischler, S. E. Kooi, V. Bulović, T. M. Swager, J. Am. Chem. Soc. 2009, 131, 5659
33. M. B. Goldfinger, K. B. Crawford, T. M. Swager, J. Am. Chem. Soc. 1997, 119, 4578
34. M. B. Goldfinger, T. M. Swager, J. Am. Chem. Soc. 1994, 116, 7895.
35. M. Hapke, K. Kral, C. Fischer, A. Spannenberg, A. Gutnov, D. Redkin, B. Heller, J. Org. Chem. 2010, 75, 3993
36. Y. Matano, M. Nakashima, H. Imahori, Angew. Chem. 2009, 121, 4062
37. Angew. Chem. Int. Ed. 2009, 48, 4002
38. P. A. Wender, J. P. Christy, A. B. Lesser, M. T. Gieseler, Angew. Chem. 2009, 121, 7823
39. Angew. Chem. Int. Ed. 2009, 48, 7687
40. S. García-Rubín, J. A. Varela, L. Castedo, C. Saá, Org. Lett. 2009, 11, 983
41. C. Zhang, D. M. Cui, L. Y. Yao, B. S. Wang, Y. Z. Hu, T. Hayashi, J. Org. Chem. 2008, 73, 7811.
42. X. Chen, H. Wang, X. Jin, J. Feng, Y. Wang, P. Lu, Chem. Commun. 2011, 47, 2628
43. R. Umeda, D. Hibi, K. Miki, Y. Tobe, Org. Lett. 2009, 11, 4104
44. Y. T. Wu, T. Hayama, K. K. Baldridge, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870
45. H. J. Knölker, A. Braier, D. J. Bröcher, P. G. Jones, H. Piotrowski, Tetrahedron Lett. 1999, 40, 8075
46. J. J. González, A. Francesch, D. J. Cárdenas, A. M. Echavarren, J. Org. Chem. 1998, 63, 2854.
47. A. Sygula, P. W. Rabideau, J. Am. Chem. Soc. 2000, 122, 6323
48. T. J. Seiders, E. L. Elliott, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc. 1999, 121, 7804
49. A. Sygula, P. W. Rabideau, J. Am. Chem. Soc. 1999, 121, 7800
50. L. T. Scott, P. C. Cheng, M. M. Hashemi, M. S. Bratcher, D. T. Meyer, H. B. Warren, J. Am. Chem. Soc. 1997, 119, 10963
51. L. T. Scott, M. M. Hashemi, D. T. Meyer, H. B. Warren, J. Am. Chem. Soc. 1991, 113, 7082.
52. Q. C. Han, Q. Su, L. Tang, J. Feng, P. Lu, Y. G. Wang, J. Phys. Chem. C 2010, 114, 18702
53. H. X. Shao, X. P. Chen, Z. X. Wang, P. Lu, J. Phys. Chem. A 2007, 111, 10386
54. Z. X. Wang, H. X. Shao, J. C. Ye, L. Tang, P. Lu, J. Phys. Chem. A 2005, 109, 19627.
55. Z. Zhao, J. H. Li, X. Chen, X. Wang, P. Lu, Y. Yang, J. Org. Chem. 2009, 74, 383
56. Z. Zhao, J. H. Li, X. Chen, P. Lu, Y. Yang, Org. Lett. 2008, 10, 3041
57. Z. Zhao, X. Xu, H. Wang, P. Lu, G. Yu, Y. Liu, J. Org. Chem. 2008, 73, 594
58. Z. Zhao, J. H. Li, P. Lu, Y. Yang, Adv. Funct. Mater. 2007, 17, 2203.
59. B. Braida, V. Prana, P. C. Hiberty, Angew. Chem. 2009, 121, 5834
60. Angew. Chem. Int. Ed. 2009, 48, 5724.
61. Y. X. Xie, Z. Y. Yan, B. Qian, W. Y. Deng, D. Z. Wang, L. Y. Wu, X. Y. Liu, Y. M. Liang, Chem. Commun. 2009, 5451
62. Y. X. Xie, X. Y. Liu, L. Y. Wu, Y. Han, L. B. Zhao, M. J. Fan, Y. M. Liang, Eur. J. Org. Chem. 2008, 1013.
63. S. Swaminathan, K. V. Narayanan, Chem. Rev. 1971, 71, 429
64. A. Arcadi, Chem. Rev. 2008, 108, 3266.
65. S. G. Wen, W. M. Liu, Y. M. Liang, J. Org. Chem. 2008, 73, 4342.
66. R. Hayashi, G. R. Cook, Tetrahedron Lett. 2008, 49, 3888
67. T. Tsubusaki, H. Nishino, Tetrahedron 2009, 65, 9448.
68. J. W. J. van Dorp, G. Lodder, J. Org. Chem. 2008, 73, 5416
69. R. Gronheid, G. Lodder, T. Okuyama, J. Org. Chem. 2002, 67, 693.
70. L. Shi, M. Horn, S. Kobayashi, H. Mayr, Chem. Eur. J. 2009, 15, 8533.
71. T. Kitamura, S. Kobayashi, H. Taniguchi, Z. Rappoport, J. Org. Chem. 1982, 47, 5003.
72. K. G. Ji, H. T. Zhu, F. Yang, X. Z. Shu, S. C. Zhao, X. Y. Liu, A. Shaukat, Y. M. Liang, Chem. Eur. J. 2010, 16, 6151.
73. J. J. Ritter, P. P. Minieri, J. Am. Chem. Soc. 1948, 70, 4045
74. J. J. Ritter, J. Kalish, J. Am. Chem. Soc. 1948, 70, 4048.
75. Baldwin's rule:, J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734.
76. S. Mehta, R. C. Larock, J. Org. Chem. 2010, 75, 1652.
77. H. Doucet, J. C. Hierso, Angew. Chem. 2007, 119, 850
78. Angew. Chem. Int. Ed. 2007, 46, 834
79. R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874.
80. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
81. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359.
82. L. Zhai, R. Shukla, R. Rathore, Org. Lett. 2009, 11, 3474
83. K. Wang, M. Lü, A. Yu, X. Zhu, Q. Wang, J. Org. Chem. 2009, 74, 935
84. B. T. King, J. Kroulík, C. R. Robertson, P. Rempala, C. L. Hilton, J. D. Korinek, L. M. Gortari, J. Org. Chem. 2007, 72, 2279.
85. J. D. Debad, J. C. Morris, V. Lynch, P. Magnus, A. J. Bard, J. Am. Chem. Soc. 1996, 118, 2374.