Furan-based o-quinodimethanes by gold-catalyzed dehydrogenative heterocyclization of 2-(1-alkynyl)-2-alken-1-ones: A modular entry to 2,3-furan-fused carbocycles

Angewandte Chemie - International Edition

Volumn 53, Issue 25, 2014, Pages 6542-6545

  Zhou, Liejin ^a   Zhang, Mingrui ^a   Li, Wenbo ^a   Zhang, Junliang ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

cycloaddition; gold; heterocycles; nitrogen oxides; synthetic methods

Indexed keywords

AROMATIC COMPOUNDS; CYCLIZATION; CYCLOADDITION; GOLD; NITROGEN OXIDES;

CARBOCYCLES; ELECTRON DEFICIENT OLEFINS; HETEROCYCLES; HETEROCYCLIZATIONS; MILD REACTION CONDITIONS; PYRIDINE N-OXIDE; SITU GENERATION; SYNTHETIC METHODS;

ORGANIC POLLUTANTS;

CYCLOPENTANE DERIVATIVE; FURAN; FURAN DERIVATIVE; GOLD;

CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROGENATION;

CYCLIZATION; CYCLOPENTANES; FURANS; GOLD; HYDROGENATION; MOLECULAR STRUCTURE;

EID: 84902344615     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201403709     Document Type: Article

References (71)

1. B. A. Keay, J. M. Hopkins, P. W. Dibble, in Comprehensive Heterocyclic Chemistry III (Eds.:, A. R. Katrizky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor,), Elsevier, Oxoford, 2008, chap. 3.08.
2. D. L. Wright, Prog. Heterocycl. Chem. 2005, 17, 1-32
3. H. N. C. Wong, K.-S. Yeung, Z. Yang, in Comprehensive Heterocyclic Chemistry III (Eds.:, A. R. Katrizky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor,), Elsevier, Oxford, 2008, chap. 3.06.
4. For recent reviews on furan synthesis, see:a) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
5. N. T. Patil, Y. Yamamoto, ARKIVOC 2007, 121-141
6. A. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657-1712
7. C. Winter, N. Krause, Chem. Rev. 2011, 111, 1994-2009
8. W. J. Moran, A. Rodríguez, Org. Prep. Proced. Int. 2012, 44, 103-130
9. A. V. Gulevich, A. S. Dudnik, N. Chernyak, V. Gevorgyan, Chem. Rev. 2013, 113, 3084-3213.
10. G. Zhang, X. Huang, G. Li, L. Zhang, J. Am. Chem. Soc. 2008, 130, 1814-1815
11. A. Aponick, C.-Y. Li, J. Malinge, E. F. Marques, Org. Lett. 2009, 11, 4624-4627
12. M. Egi, K. Azechi, S. Akai, Org. Lett. 2009, 11, 5002-5005
13. S. Kramer, J. L. H. Madsen, M. Rottländer, T. Skrydstrup, Org. Lett. 2010, 12, 2758-2761
14. A. Dudnik, Y. Xia, Y. Li, V. Gevorgyan, J. Am. Chem. Soc. 2010, 132, 7645-7655
15. T. Wang, S. Shi, M. M. Hansmann, E. Rettenmeier, M. Rudolph, A. S. K. Hashmi, Angew. Chem. 2014, 126, 3789-3793
16. Angew. Chem. Int. Ed. 2014, 53, 3715-3719; for synthesis of 2,3-furan-fused carbocyles
17. A. S. K. Hashmi, P. Haufe, C. Schmid, A. Rivas Nass, W. Frey, Chem. Eur. J. 2006, 12, 5376-5382
18. A. S. K. Hashmi, M. C. Blanco, E. Kurpejovic̈, W. Frey, J. W. Bats, Adv. Synth. Catal. 2006, 348, 709-713
19. Z. Dong, C.-H. Liu, Y. Wang, M. Lin, Z.-X. Yu, Angew. Chem. 2013, 125, 14407-14411
20. Angew. Chem. Int. Ed. 2013, 52, 14157-14161, and references therein.
21. V. Benešová, Z. Samek, V. Herout, F. Šorm, Collect. Czech. Chem. Commun. 1969, 34, 582-592
22. H. Tazaki, H. Soutome, K. Nabeta, H. Okuyama, H. Becker, Phytochemistry 1996, 42, 465-468
23. O. Richou, V. Vaillancourt, D. J. Faulkner, K. F. Albizati, J. Org. Chem. 1989, 54, 4729-4730
24. P. Torres, J. Ayala, C. Grande, J. Anaya, M. Grande, Phytochemistry 1999, 52, 1507-1513
25. E. P. Kündig, R. Cannas, M. Laxmisha, L. Ronggang, S. Tchertchian, J. Am. Chem. Soc. 2003, 125, 5642-5643.
26. For reviews on o-QDMs:a) N. Martín, C. Seoane, M. Hanack, Org. Prep. Proc. Int. 1991, 23, 237-272
27. H. Nemoto, K. Fukumoto, Tetrahedron 1998, 54, 5425-5464
28. J. L. Segura, N. Martín, Chem. Rev. 1999, 99, 3199-3246; for the first example of o-QDM, see
29. M. P. Cava, D. R. Napier, J. Am. Chem. Soc. 1957, 79, 1701-1705; for recent examples, see
30. B. Grosch, C. N. Orlebar, E. Herdtweck, W. Massa, T. Bach, Angew. Chem. 2003, 115, 3822-3824
31. Angew. Chem. Int. Ed. 2003, 42, 3693-3696
32. A. Ouchi, Z. Li, M. Sakuragi, T. Majima, J. Am. Chem. Soc. 2003, 125, 1104-1108
33. Y. Matsuya, N. Ohsawa, H. Nemoto, J. Am. Chem. Soc. 2006, 128, 412-413
34. R. Kuwano, T. Shige, J. Am. Chem. Soc. 2007, 129, 3802-3803
35. H. Yoshida, S. Nakano, M. Mukae, J. Ohshita, Org. Lett. 2008, 10, 4319-4322
36. S. Ueno, M. Ohtsubo, R. Kuwano, J. Am. Chem. Soc. 2009, 131, 12904-12905
37. H. Yoshida, M. Mukae, J. Ohshita, Chem. Commun. 2010, 46, 5253-5255
38. S. Ueno, M. Ohtsubo, R. Kuwano, Org. Lett. 2010, 12, 4332-4334
39. S. F. Zhu, R. X. Liang, H. F. Jiang, W. Q. Wu, Angew. Chem. 2012, 124, 11019-11023
40. Angew. Chem. Int. Ed. 2012, 51, 10861-10865.
41. For general reviews on heteroaromatic oQDMs, see:a) T. S. Chou, Rev. Heteroat. Chem. 1993, 8, 65-104
42. S. J. Collier, R. C. Storr, in Progress in Heterocyclic Chemistry, Vol. 10 (Eds.:, G. W. Gribble, T. L. Gilchrist,), Pergamon, New York, 1998, pp. 25-48; Magnus and co-workers have done seminal work in developing an indole-2,3-quinodimethane strategy in total synthesis. See
43. P. Magnus, T. Gallagher, P. Brown, P. Pappalardo, Acc. Chem. Res. 1984, 17, 35-41; for a review of indole-2,3-quinodimethanes, see
44. U. Pindur, H. Erfanian-Abdoust, Chem. Rev. 1989, 89, 1681-1689; for recent examples, see
45. N. Kuroda, Y. Takahashi, K. Yoshinaga, C. Mukai, Org. Lett. 2006, 8, 1843-1845
46. Y. Liu, M. Nappi, E. Arceo, S. Vera, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 15212-15218
47. Y.-C. Xiao, Q.-Q. Zhou, L. Dong, T.-Y. Liu, Y.-C. Chen, Org. Lett. 2012, 14, 5940-5943
48. S. Zhao, R. B. Andrade, J. Am. Chem. Soc. 2013, 135, 13334-13337.
49. G.-B. Liu, H. Mori, S. Katsumura, Chem. Commun. 1996, 2251-2252.
50. W. S. Trahanovsky, T. J. Cassady, T. L. Woods, J. Am. Chem. Soc. 1981, 103, 6691-6695
51. C.-H. Chou, W. S. Trahanovsky, J. Am. Chem. Soc. 1986, 108, 4138-4144
52. M.-K. Leung, W. S. Trahanovsky, J. Am. Chem. Soc. 1995, 117, 841-850.
53. For metal-catalyzed reactions, see:a) T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164-11165
54. N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem. 2005, 70, 4531-4534; for selected work from our group, see
55. Y. Xiao, J. Zhang, Angew. Chem. 2008, 120, 1929-1932
56. Angew. Chem. Int. Ed. 2008, 47, 1903-1906
57. F. Liu, D. Qian, L. Li, X. Zhao, J. Zhang, Angew. Chem. 2010, 122, 6819-6822
58. Angew. Chem. Int. Ed. 2010, 49, 6669-6672
59. Z.-M. Zhang, P. Chen, W. Li, Y. Niu, X. L. Zhao, J. Zhang, Angew. Chem. 2014, 126, 4439-4443
60. Angew. Chem. Int. Ed. 2014, 53, 4350-4354
61. G. Zhou, F. Liu, J. Zhang, Chem. Eur. J. 2011, 17, 3101-3104.
62. Selected transformations without a metal catalyst, see:a) Y. H. Liu, S. Zhou, Org. Lett. 2005, 7, 4609-4611
63. T. Yao, X. Zhang, R. C. Larock, J. Org. Chem. 2005, 70, 7679-7686
64. L. Zhao, F. Xie, G. Cheng, Y. Hu, Angew. Chem. 2009, 121, 6642-6645
65. Angew. Chem. Int. Ed. 2009, 48, 6520-6523
66. W. Li, J. Zhang, Org. Lett. 2014, 16, 162-165, and references therein.
67. Y. Wang, A. Yepremyan, S. Ghorai, R. Todd, D. H. Aue, L. Zhang, Angew. Chem. 2013, 125, 7949-7953
68. Angew. Chem. Int. Ed. 2013, 52, 7795-7799
69. L. Ye, Y. Wang, D. H. Aue, L. Zhang, J. Am. Chem. Soc. 2012, 134, 31-34.
70. C.-M. Ting, Y.-L. Hsu, R.-S. Liu, Chem. Commun. 2012, 48, 6577-6579.
71. CCDC 984637 (3b), 984638 (7), 984633 (10b), 984634 (12a), and 984635 (13) contain 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.