Gold(i)-catalyzed 1,4- And/or 1,5-heteroaryl migration reactions through regiocontrolled cyclizations

Chemistry - A European Journal

Volumn 21, Issue 2, 2015, Pages 559-564

  Wang, Chengyu ^a,b   Xie, Xin ^a   Liu, Jun ^a   Liu, Yuanhong ^a   Li, Yuxue ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

Alkenes; Furans; Gold catalysis; Migration; Stereoselectivity

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; GOLD; HYDROCARBONS; MOLECULAR SIEVES; OLEFINS; ORGANIC POLLUTANTS; SIEVES; STEREOSELECTIVITY;

CYCLOISOMERIZATIONS; EXO-CYCLIZATION; FURANS; GOLD CATALYSIS; MIGRATION; MIGRATION REACTION; REGIO-SELECTIVE; TRISUBSTITUTED ALKENES;

CYCLIZATION;

ALKENE; FURAN; FURAN DERIVATIVE; GOLD;

CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

ALKENES; CATALYSIS; CYCLIZATION; FURANS; GOLD; STEREOISOMERISM;

EID: 84920167852     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201405190     Document Type: Article

References (59)

1. a) B. H. Lipshutz, Chem. Rev. 1986, 86, 795;
2. b) H. Heaney, J. S. Ahn in Comprehensive Heterocyclic Chemistry II, Vol. 2 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, pp. 297-350;
3. c) J. A. Joule, K. Mills, Heterocyclic Chemistry, 5th ed., Wiley-Blackwell, Hoboken, 2010, pp. 347-368.
4. a) A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553;
5. b) A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769;
6. c) A. S. K. Hashmi, L. Ding, J. W. Bats, P. Fischer, W. Frey, Chem. Eur. J. 2003, 9, 4339;
7. d) A. S. K. Hashmi, J. P. Weyrauch, M. Rudolph, E. Kurpejović, Angew. Chem. Int. Ed. 2004, 43, 6545;
8. Angew. Chem. 2004, 116, 6707;
9. e) A. S. K. Hashmi, M. Rudolph, J. P. Weyrauch, M. Wölfle, W. Frey, J. W. Bats, Angew. Chem. Int. Ed. 2005, 44, 2798;
10. Angew. Chem. 2005,117, 2858;
11. f) A. S. K. Hashmi, P. Haufe, C. Schmid, A. R. Nass, W. Frey, Chem. Eur. J. 2006, 12, 5376;
12. g) A. S. K. Hashmi, M. C. Blanco, E. Kurpejović, W. Frey, J. W. Bats, Adv. Synth. Catal. 2006, 348, 709;
13. h) A. S. K. Hashmi, M. Rudolph, J. W. Bats, W. Frey, F. Rominger, T. Oeser, Chem. Eur. J. 2008, 14, 6672;
14. i) A. S. K. Hashmi, M. Rudolph, H. Siehl, M. Tanaka, J. W. Bats, W. Frey, Chem. Eur. J. 2008, 14, 3703;
15. j) A. S. K. Hashmi, S. Pankajakshan, M. Rudolph, E. Enns, T. Bander, F. Rominger, W. Frey, Adv. Synth. Catal. 2009, 351, 2855;
16. k) A. S. K. Hashmi, M. Wölfle, F. Ata, W. Frey, F. Rominger, Synthesis 2010, 2297.
17. a) Y. Chen, Y. Lu, G. Li, Y. Liu, Org. Lett. 2009, 11, 3838;
18. b) A. S. K. Hashmi, M. Rudolph, J. Huck, W. Frey, J. W. Bats, M. Hamzić, Angew. Chem. Int. Ed. 2009, 48, 5848;
19. Angew. Chem. 2009, 121, 5962;
20. c) Y. Chen, G. Li, Y. Liu, Adv. Synth. Catal. 2011, 353, 392;
21. d) Y. Chen, Y. Liu, J. Org. Chem. 2011, 76, 5274;
22. e) A. S. K. Hashmi, W. Yang, F. Rominger, Angew. Chem. Int. Ed. 2011, 50, 5762;
23. Angew. Chem. 2011, 123, 5882;
24. f) C. Wang, Y. Chen, X. Xie, J. Liu, Y. Liu, J. Org. Chem. 2012, 77, 1915;
25. g) A. S. K. Hashmi, W. Yang, F. Rominger, Chem. Eur. J. 2012, 18, 6576;
26. h) N. Sun, X. Xie, Y. Liu, Chem. Eur. J. 2014, 20, 7514;
27. i) Y. Chen, L. Wang, N. Sun, X. Xie, X. Zhou, H. Chen, Y. Li, Y. Liu, Chem. Eur. J. 2014, 20, 12015.
28. a) R. S. Menon, M. G. Banwell, Org. Biomol. Chem. 2010, 8, 5483;
29. b) Z. Dong, C. H. Liu, Y. Wang, M. Lin, Z. X. Yu, Angew. Chem. Int. Ed. 2013, 52, 14157;
30. Angew. Chem. 2013, 125, 14407.
31. a) S. G. Modha, A. Kumar, D. D. Vachhani, S. K. Sharma, V. S. Parmar, E. V. Van der Eycken, Chem. Commun. 2012, 48, 10916;
32. b) A. Kumar, Z. Li, S. K. Sharma, V. S. Parmar, E. V. Van der Eycken, Chem. Commun. 2013, 49, 6803;
33. c) A. Kumar, D. D. Vachhani, S. G. Modha, S. K. Sharma, V. S. Parmar, E. V. van der Eycken, Synthesis 2013, 45, 2571.
34. a) A. S. K. Hashmi, T. Häffner, W. Yang, S. Pankajakshan, S. Schäfer, L. Schultes, F. Rominger, W. Frey, Chem. Eur. J. 2012, 18, 10480;
35. b) A. S. K. Hashmi, J. Hofmann, S. Shi, A. Schütz, M. Rudolph, C. Lothschütz, M. Wieteck, M. Bührle, M. Wölfle, F. Rominger, Chem. Eur. J. 2013, 19, 382.
36. a) A. Studer, M. Bossart, Tetrahedron 2001, 57, 9649,
37. b) A. Studer, M. Bossart, T. Vasella, Org. Lett. 2000, 2, 985;
38. c) K. Wakabayashi, H. Yorimitsu, H. Shinokubo, K. Oshima, Org. Lett. 2000, 2, 1899;
39. d) A. Gheorghe, B. Quic-let-Sire, X. Vila, S. Z. Zard, Org. Lett. 2005, 7, 1653;
40. e) S. Amrein, M. Bossart, T. Vasella, A. Studer, J. Org. Chem. 2000, 65, 4281.
41. a) J. W. Wilt, T. P. Malloy, J. Am. Chem. Soc. 1970, 92, 4747;
42. b) J. W. Wilt, T. P. Malloy, P. K. Mookerjee, D. R. Sullivan, J. Org. Chem. 1974, 39, 1327;
43. c) K. Tomooka, A. Nakazaki, T. Nakai, J. Am. Chem. Soc. 2000, 122, 408;
44. d) T. Khan, P. J. Skabara, S. J. Coles, M. B. Hursthouse, Chem. Commun. 2001, 369;
45. e) A. Nakazaki, J. Usuki, K. Tomooka, Synlett 2008, 2064;
46. f) L. Wu, M. Shi, Y. Li, Chem. Eur. J. 2010, 16, 5163.
47. Y. Chen, L. Wang, Y. Liu, Y. Li, Chem. Eur. J. 2011, 17, 12582.
48. CCDC-915008 (2a), -1023011 (3d), -915006 (5), -915009 (9), and -915007 (17) 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.
49. a) P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136, B864-B871;
50. )W. Kohn, L. J. Sham, Phys. Rev. 1965, 140, A1133-A1138.
51. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, A., Jr., Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT, 2009.
52. a) J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865;
53. b) J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1997, 78, 1396.
54. R. H. Kang, H. Chen, S. Shaik, J. N. Yao, J. Chem. Theory Comput. 2011, 7, 4002.
55. P. Fuentealba, H. Preuss, H. Stoll, L. von Szentpály, Chem. Phys. Lett. 1982, 89, 418.
56. a) N. A. Petasis, S. P. Lu, J. Am. Chem. Soc. 1995, 117, 6394;
57. b) N. A. Petasis, S. P. Lu, Tetrahedron Lett. 1996, 37, 141. For DFT study on the reaction mechanism, see:
58. c) G. J. Jiang, Y. Wang, Z. X. Yu, J. Org. Chem. 2013, 78, 6947.
59. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.