Copper-catalyzed radical reaction of N -tosylhydrazones: Stereoselective synthesis of (E)-vinyl sulfones

Organic Letters

Volumn 17, Issue 7, 2015, Pages 1692-1695

  Mao, Shuai ^a   Gao, Ya Ru ^a   Zhu, Xue Qing ^a   Guo, Dong Dong ^a   Wang, Yong Qiang ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84926479440     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00461     Document Type: Article

References (86)

1. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236
2. Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. 2012, 48, 10162
3. Enders, D.; Wortmann, L.; Peters, R. Acc. Chem. Res. 2000, 33, 157
4. Lazny, R.; Nodzewska, A. Chem. Rev. 2010, 110, 1386
5. Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626
6. Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges 1883, 16, 6
7. Fischer, E.; Hess, O. Ber. Dtsch. Chem. Ges 1884, 17, 559
8. Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons: Chichester, 1982.
9. Kishner, N. Zh. Russ. Fiz.-Khim. O-va., Chast. Khim. 1911, 43, 582
10. Wolff, L. Justus Liebigs Ann. Chem. 1912, 394, 86
11. Barluenga, J.; Vald, C. Angew. Chem., Int. Ed. 2011, 50, 7486
12. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560
13. Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024
14. Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586
15. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
16. Davies, H. M. L.; Denton, J. R. Chem. Soc. Rev. 2009, 38, 3061
17. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704
18. Slattery, C. N.; Ford, A.; Maguire, A. R. Tetrahedron 2010, 66, 6681
19. Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857
20. Jellema, E.; Jongerius, A. L.; Reek, J. N. H.; de Bruin, B. Chem. Soc. Rev. 2010, 39, 1706
21. Zhu, S.-F.; Cai, Y.; Mao, H.-X.; Xie, J.-H.; Zhou, Q.-L. Nat. Chem. 2010, 2, 546
22. Doyle, M. P.; Ratnikov, M.; Liu, Y. Org. Biomol. Chem. 2011, 9, 4007
23. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977
24. Doyle, M. P. Angew. Chem., Int. Ed. 2009, 48, 850
25. Davies, P. W.; Albrecht, S. J.-C. Angew. Chem., Int. Ed. 2009, 48, 8372
26. Padwa, A. Chem. Soc. Rev. 2009, 38, 3072
27. Sweeney, J. B. Chem. Soc. Rev. 2009, 38, 1027
28. Zhang, Y.; Wang, J. Coord. Chem. Rev. 2010, 254, 941
29. Barluenga, J.; Tomas-Gamasa, M.; Aznar, F.; Valdes, C. Angew. Chem., Int. Ed. 2010, 49, 4993
30. Valdes, C. Angew. Chem., Int. Ed. 2012, 51, 5953
31. Barluenga, J.; Tomas-Gamasa, M.; Valdes, C. Angew. Chem., Int. Ed. 2012, 51, 5950
32. Li, H.; Wang, L.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 2943
33. Bruneau, C. Angew. Chem., Int. Ed. 2005, 44, 2328
34. Marco-Contelles, J.; Soriano, E. Chem.-Eur. J. 2007, 13, 1350
35. Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750
36. Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011, 1015
37. Peng, C.; Wang, Y.; Wang, J. J. Am. Chem. Soc. 2008, 130, 1566
38. Kudirka, R.; Devine, S. K. J. C.; Adams, S.; Van Vranken, D. L. Angew. Chem., Int. Ed. 2009, 48, 3677
39. Zhang, Z.; Liu, Y.; Gong, M.; Zhao, X.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2010, 49, 1139
40. Feng, X.-W.; Wang, J.; Zhang, J.; Yang, J.; Wang, N.; Yu, X.-Q. Org. Lett. 2010, 12, 4408
41. Tsoi, Y.-T.; Zhou, Z.; Yu, W.-Y. Org. Lett. 2011, 13, 5370
42. Chen, Z.-S.; Duan, X.-H.; Wu, L.-Y.; Ali, S.; Ji, K.-G.; Zhou, P.-X.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2011, 17, 6918
43. Yang, K.; Zhang, J.; Li, Y.; Cheng, B.; Zhao, L.; Zhai, H. Org. Lett. 2013, 15, 808
44. 3 (3 equiv) in dioxane at 100 °C for 8-12 h. Ojha, D. P.; Prabhu, K. R. Org. Lett. 2015, 17, 18-21
45. Noshi, M. N.; El-awa, A.; Torres, E.; Fuchs, P. L. J. Am. Chem. Soc. 2007, 129, 11242
46. Desrosiers, J.-N.; Charette, A. B. Angew. Chem., Int. Ed. 2007, 46, 5955
47. Reddy, M. V.; Iqbal, N. M.; Robell, K. A.; Kang, A. D.; Reddy, E. P. J. Med. Chem. 2008, 51, 86
48. Zhu, Q.; Lu, Y. Org. Lett. 2009, 11, 1721
49. Newton, A. S.; Glória, P. M. C.; Gonçalves, L. M.; Santos, D. J. V. A.; Moreira, R.; Guedes, R. C.; Santos, M. M. M. Eur. J. Med. Chem. 2010, 45, 3858
50. Mertens, M. D.; Schmitz, J.; Horn, M.; Furtmann, N.; Bajorath, J.; Mares, M.; Gütschow, M. ChemBioChem 2014, 15, 955
51. Meadows, D. C.; Mathews, T. B.; North, T. W.; Hadd, M. J.; Kuo, C. L.; Neamati, N.; Gervay-Hague, J. J. Med. Chem. 2005, 48, 4526
52. Kisselev, A. F.; Goldberg, A. L. Chem. Biol. 2001, 8, 739
53. Li, H.; Song, J.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2005, 127, 8948
54. Sulzer-Mossé, S.; Alexakis, A.; Mareda, J.; Bollot, G.; Bernardinelli, G.; Filinchuk, Y. Chem.-Eur. J. 2009, 15, 3204
55. Pal, T.; Dey, S.; Pathak, T. J. Org. Chem. 2011, 76, 3034
56. Llamas, T.; Arrayás, R. G.; Carretero, J. C. Org. Lett. 2006, 8, 1795
57. Sahu, D.; Dey, S.; Pathak, T.; Ganguly, B. Org. Lett. 2014, 16, 2100
58. Trost, B. M.; Ghadiri, M. R. J. Am. Chem. Soc. 1986, 108, 1098
59. Nájera, C.; Yus, M. Tetrahedron 1999, 55, 10547
60. Das, I.; Pathak, T. Org. Lett. 2006, 8, 1303
61. Baskin, J. M.; Wang, Z. Org. Lett. 2002, 4, 4423
62. Matteucci, M.; Bhalay, G.; Bradley, M. Org. Lett. 2003, 5, 235
63. Huang, X.; Duan, D.; Zheng, W. J. Org. Chem. 2003, 68, 1958
64. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L. M.; Bernini, R. J. Org. Chem. 2004, 69, 5608
65. Zhu, W.; Ma, D. J. Org. Chem. 2005, 70, 2696
66. Huang, F.; Batey, R. A. Tetrahedron 2007, 63, 7667
67. Guan, Z.-H.; Zuo, W.; Zhao, L.-B.; Ren, Z.-H.; Liang, Y.-M. Synthesis 2007, 1465
68. Reeves, D. C.; Rodriguez, S.; Lee, H.; Hahhad, N.; Krishnamurthy, D.; Senanayake, C. H. Tetrahedron Lett. 2009, 50, 2870
69. Das, B.; Lingaiah, M.; Damodar, K.; Bhunia, N. Synthesis 2011, 2941
70. Liang, S.; Zhang, R.-Y; Wang, G.; Chen, S.-Y.; Yu, X.-Q. Eur. J. Org. Chem. 2013, 7050
71. Neo, A. G.; López, C.; Romero, V.; Antelo, B.; Delamano, J.; Pérez, A.; Fernandez, D.; Almeida, J. F.; Castedo, L.; Tojo, G. J. Org. Chem. 2010, 75, 6764
72. Rajkumar, S.; Shankland, K.; Goodman, J. M.; Cobb, A. J. Org. Lett. 2013, 15, 1386
73. Chang, M.-Y.; Chen, Y.-C.; Lin, S.-Y.; Chan, C.-K. Tetrahedron 2014, 70, 1740
74. Taniguchi, N. Tetrahedron 2014, 70, 1984
75. Shelke, G. M.; Rao, V. K.; Pericherla, K.; Kumar, A. Synlett 2014, 25, 2345
76. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079 and references therein
77. Hintermann, L.; Labonne, A. Synthesis 2007, 1121
78. Rao, K.; Prasad, P.; Lingaiah, N. Green Chem. 2012, 14, 1507
79. Nairoukh, Z.; Avnir, D.; Blum, J. ChemSusChem 2013, 6, 430
80. Negishi, E.; King, A. O.; Klima, W. L.; Patterson, W.; Silveira, A., Jr. J. Org. Chem. 1980, 45, 2526
81. Lalezari, I.; Shafiee, A.; Yalpani, M. Angew. Chem., Int. Ed. 1970, 9, 464
82. Scannell, R. T.; Stevenson, R. J. Heterocycl. Chem. 1980, 17, 1727
83. Lyapkalo, I. M.; Vogel, M. A. K. Angew. Chem., Int. Ed. 2006, 45, 4019
84. Li, X.; Liu, X.; Chen, H.; Wu, W.; Qi, C.; Jiang, H. Angew. Chem., Int. Ed. 2014, 53, 14485
85. Dewey, R. S.; van Tamelen, E. E. J. Am. Chem. Soc. 1961, 83, 3729
86. Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem., Int. Ed. 2014, 53, 4205