Iron-catalyzed regioselective hydroaryloxylation of C≡C Triple Bonds: An efficient synthesis of 2H-1-benzopyran derivatives

Advanced Synthesis and Catalysis

Volumn 351, Issue 16, 2009, Pages 2599-2604

  Xu, Xiaobing ^a   Liu, Jun ^a   Liang, Linfeng ^a   Li, Hongfeng ^a   Li, Yanzhong ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Benzopyrans; Hydroaryloxylation; Iron catalysis; Naphthopyrans; Regioselective cyclization

Indexed keywords

EID: 70649107049     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900483     Document Type: Article

References (86)

1. For selected examples, see a) S. Seo, X. Yu, T. J. Marks, J. Am. Chem. Soc. 2009, 131, 263;
2. b) A. Dzudza, T. J. Marks, Org. Lett. 2009, 11, 1523;
3. c) X. Yu, S. Seo, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 7244;
4. d) J. Barluenga, A. Fernandez, A. Satrustegui, A. Dieguez, F. Rodriguez, J. Fananas, Chem. Eur. J. 2008, 14, 4153;
5. e) L. A. Adrio, K. K. Hii, Chem. Commun. 2008, 2325;
6. f) L. Coulombel, M. Rajzmann, J.-M. Pons, S. Olivero, E. Dunach, Chem. Eur. J. 2006, 12, 6356;
7. g) C.-G. Yang, C. He, J. Am. Chem. Soc. 2005, 127, 6966;
8. h) Y. Oe, T. Ohta, Y. Ito, Synlett 2005, 1, 179;
9. i) H. Qian, X. Han, R. A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 9536;
10. j) K. Komeyama, T. Morimoto, Y. Nakayama, K. Takaki, Tetrahedron Lett. 2007, 48, 3259;
11. k) C.-G. Yang, N. W. Reich, Z. Shi, Org. Lett. 2005, 7, 4553;
12. l) D. C. Rosenfeld, S. Shekhar, A. Takemiya, M. Utsunomiya, J. F. Hartwig, Org. Lett. 2006, 8, 4179;
13. m) R. V. Nguyen, X. Q. Yao, C. J. Li, Org. Lett. 2006, 8, 2397;
14. n) S. W. Youn, J. I. Eom, J. Org. Chem. 2006, 71, 6705;
15. o) L. Coulombel, I. Favier, E. Dunach, Chem. Commun. 2005, 2286;
16. p) Y. Nishibayashi, Y. Inada, M. Yoshikawa, M. Hidai, S. Uemura, Angew. Chem. 2003, 115, 1533;
17. Angew. Chem. Int. Ed. 2003, 42, 1495;
18. q) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079, and references cited therein;
19. r) Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett. 2005, 7, 5409.
20. a) P. J. Brogden, C. D. Gabbutt, J. D. Hepworth, Pyrans and Fused Pyrans, in: Comprehensive Heterocyclic Chemistry, (Ed.: A. Katrizky), Pergamon Press, Oxford, 1984, Vol.3, p 573;
21. b) P. N. Confalone, J. Heterocycl. Chem. 1990, 27, 31;
22. c) R. H. Cichewicz, V. A. Kenyon, S. Whitman, N. M. Morales, J. F. Arguello, T. R. Holman, P. Crews, J. Am. Chem. Soc. 2004, 126, 14911;
23. d) W. Pongcharoen, V. Rukachaisirikul, S. Phongpaichit, J. Sakayaroj, Chem. Pharm. Bull. 2007, 55, 1404;
24. e) S. C. Pelly, S. Govender, M. A. Fernandes, H. G. Schmalz, C. B. de Koning, J. Org. Chem. 2007, 72, 2857.
25. a) S. W. Youn, S. J. Pastine, D. Sames, Org. Lett. 2004, 6, 581;
26. b) S. J. Pastine, S. W. Youn, D. Sames, Org. Lett. 2003, 5, 1055;
27. c) S. J. Pastine, S. W. Youn, D. Sames, Tetrahedron 2003, 59, 8859;
28. d) Y.-W. Dong, G.-W. Wang, L. Wang, Tetrahedron 2008, 64, 10148;
29. e) V. H. Grant, B. Liu, Tetrahedron Lett. 2005, 46, 1237.
30. a) Y.-C. Wu, L. Liu, Y.-L. Liu, D. Wang, Y.-J. Chen, J. Org. Chem. 2007, 72, 9383;
31. b) Y. Ishino, M. Mihara, N. Hayakawa, T. Miyata, Y. Kaneko, T. Miyata, Synth. Commun. 2001, 31, 439;
32. c) F. Bigi, S. Carloni, R. Maggi, C. Muchetti, G. Sartori, J. Org. Chem. 1997, 62, 7024;
33. d) K. Tanaka, H. Aoki, H. Hosomi, S. Ohba, Org. Lett. 2000, 2, 2133.
34. a) C. D. Gabbutt, B. M. Heron, A.C. Instone, D. A. Thomas, S. M. Partington, M. B. Hursthouse, T. Gelbrich, Eur. J. Org. Chem. 2003,1220;
35. b) W. Zhao, E. M. Carreira, Org. Lett. 2003, 5, 4153.
36. For selected examples see : a) C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217;
37. b) A. Furstner, R. Martin, Chem. Lett. 2005, 34, 624;
38. c) B. D. Sherry, A. Furstner, Ace. Chem. Res. 2008, 41, 1500, and references cited therein;
39. d) C. M. R. , P. Vogel, Angew. Chem. 2008, 120, 1325;
40. Angew. Chem. Int. Ed. 2008, 47, 1305;
41. e) J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 5858;
42. f) G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 4442;
43. Angew. Chem. Int. Ed. 2007, 46, 4364;
44. g) R. R. Chowdhury, A. K. Crane, C. Fowler, P. Kwong, C. M. Kozak, Chem. Commun. 2008, 94;
45. h) W. Liu, A. Lei, Tetrahedron Lett. 2008, 49, 610;
46. i) T. Hatakeyama, M. Nakamura, J. Am. Chem. Soc. 2007, 129, 9844;
47. j) Z. Lu, G. Chai, S. Ma, J. Am. Chem. Soc. 2007, 129, 14546;
48. k) G. Cahiez, A. Moyeux, J. Buendia, C. Duplais, J. Am. Chem. Soc. 2007, 129, 13788;.
49. a) T. Hatakeyama, Y. Yoshimoto, T. Gabriel, M. Nakamura, Org. Lett. 2008, 10, 5341;
50. b) A. Fuerstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W Lehmann, J. Am. Chem. Soc. 2008, 130, 8773;
51. c) J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 5858;
52. d) P. Le Marquand, G. C. Tsui, J. C. C. Whitney, W. Tarn, J. Org. Chem. 2008, 73, 7829;
53. e) T. Hata, N. Hirone, S. Sujaku, K. Nakano, H. Urabe, Org. Lett. 2008, 10, 5031;
54. f) G. Cahiez, O. Gager, V. Habiak, Synthesis 2008, 2636;
55. g) G. Cahiez, V. Habiak, O. Gager, Org. Lett. 2008, 10, 2389.
56. a) A. Correa, O. G. Mancheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108, and references cited therein;
57. b) S. Enthaler, K. Junge, M. Bélier, Angew. Chem. 2008, 120, 3363;
58. Angew. Chem. Int. Ed. 2008, 47, 3317;
59. c) D. Guo, H. Huang, J. Xu, H. Jiang, H. Liu, Org. Lett. 2008, 10, 4513;
60. d) N. Xia, M. Taillefer, Chem. Eur. J. 2008, 14, 6037;
61. e) B. Moreau, J. Y. Wu, T. Ritter, Org. Lett. 2009, 11, 337;
62. f) Z. Li, R. Yu, H. Li, Angew. Chem. 2008, 120, 7607;
63. Angew. Chem. Int. Ed. 2008, 47, 7497;
64. g) Y. Yang, E. A. F. Foryce, F. Y. Chen, H. W. Lam, Angew. Chem. 2008, 120, 7460;
65. Angew. Chem. Int. Ed. 2008, 47, 7350.
66. a) A. Correa, C. Bolm, Angew. Chem. 2007, 119, 9018;
67. Angew. Chem. Int. Ed. 2007, 46, 8862;
68. b) A. Correa, C. Bolm, Adv. Synth. Catal. 2008, 350, 391;
69. c) A. Correa, S. Elmore, C. Bolm, Chem. Eur. J. 2008, 14, 3527;
70. d) M. Nakanishi, A.-F. Salit, C. Bolm, Adv. Synth. Catal. 2008, 350, 1835;
71. e) O. Bistri, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 596;
72. Angew. Chem. Int. Ed. 2008, 47, 586;
73. f) J. Bonnamour, C. Bolm, Org. Lett. 2008, 10, 2665;
74. g) A. Correa, M. Carril, C. Bolm, Angew. Chem. 2008, 120, 2922;
75. Angew. Chem. Int. Ed. 2008, 47, 2880;
76. h) M. Carril, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 4940;
77. Angew. Cnem. Int. Ed. 2008, 47, 4862.
78. a) X. Yuan, X. Xu, X. Zhou, J. Yuan, L. Mai, Y. Li, J. Org. Chem. 2007, 72, 1510;
79. b) X. Xu, J. Yang, L. Liang, J. Liu, L. Mai, Y. Li, Tetrahedron Lett. 2009, 50, 57;
80. c) X. Zhou, H. Zhang, J. Yuan, L. Mai, Y. Li, Tetrahedron Lett. 2007, 48, 7236;
81. d) K. Kanno, S. Ren, Y. Li, K. Nakajima, T. Takahashi, Tetrahedron Lett. 2007, 48, 9199;
82. e) H. Li, J. Liu, B. Yan, Y. Li, Tetrahedron Lett. 2009, 50, 2353.
83. J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734.
84. a) H. Harkat, A. Blanc, J.-M. Weibel, R. Pale, J. Org. Chem. 2008, 73, 1620;
85. b) Y.-C. Wu, L. Liu, Z. Shafiq, Y.-C. Wu, D. Wang, Y.-J. Chen, Synthesis 2007, 1961 and references cited therein.
86. CCDC 739832 (2a) 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 or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 IEZ, UK; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk.