Regioselective Synthesis of Vinyl Halides, Vinyl Sulfones, and Alkynes: A Tandem Intermolecular Nucleophilic and Electrophilic Vinylation of Tosylhydrazones

Organic Letters

Volumn 17, Issue 1, 2015, Pages 18-21

  Ojha, Devi Prasan ^a   Prabhu, Kandikere Ramaiah ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84926472888     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503114n     Document Type: Article

References (57)

1. Barton, D. H. R.; O'Brien, R. E.; Sternhell, S. J. Chem. Soc. 1962, 470
2. Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron Lett. 1983, 24, 1605
3. Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron 1988, 44, 147
4. Furrow, M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 5436
5. Barluenga, J.; Tomás-Gamasa, M.; Aznar, F.; Valdés, C. Nat. Chem. 2009, 1, 494
6. Peng, C.; Zhang, W.; Yan, G.; Wang, J. Org. Lett. 2009, 11, 1667
7. Li, X.; Feng, Y.; Lin, L.; Zou, G. J. Org. Chem. 2012, 77, 10991
8. Li, H.; Wang, L.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 2943
9. Li, H.; Shangguan, X.; Zhang, Z.; Huang, S.; Zhang, Y.; Wang, J. Org. Lett. 2014, 16, 448
10. Lin, Y.; Luo, P.; Zheng, Q.; Liu, Y.; Sanga, X.; Ding, Q. RSC Adv. 2014, 4, 16855
11. Sha, Q.; Wei, Y. Org. Biomol. Chem. 2013, 11, 5615
12. García-Muñoz, A.; Tomás-Gamasa, M.; Pérez-Aguilar, M. C.; Cuevas-Yañez, E.; Valdés, C. Eur. J. Org. Chem. 2012, 3925
13. Ding, Q.; Cao, B.; Yuan, J.; Liua, X.; Peng, Y. Org. Biomol. Chem. 2011, 9, 748
14. Barluenga, J.; Tomás-Gamasa, M.; Aznar, F.; Valdés, C. Angew. Chem., Int. Ed. 2010, 49, 4993
15. Barluenga, J.; Tomás-Gamasa, M.; Valdés, C. Angew. Chem., Int. Ed. 2012, 51, 5950
16. Yadav, A. K.; Srivastava, V. P.; Yadav, L. D. S. Chem. Commun. 2013, 49, 2154
17. Barluenga, J.; Quiñones, N.; Tomás-Gamasa, M.; Cabal, M.-P. Eur. J. Org. Chem. 2012, 2312
18. Pérez-Aguilar, M. C.; Valdés, C. Angew. Chem., Int. Ed. 2012, 51, 5953
19. Allwood, D. M.; Blakemore, D. C.; Ley, S. V. Org. Lett. 2014, 16, 3064
20. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486
21. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560
22. Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586
23. Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024
24. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236
25. Taber, D. F.; Guo, P. J. Org. Chem. 2008, 73, 9479
26. Taber, D. F.; Guo, P.; Guo, N. J. Am. Chem. Soc. 2010, 132, 11179
27. Ojha, D. P.; Prabhu, K. R. J. Org. Chem. 2013, 78, 12136
28. Ojha, D. P.; Prabhu, K. R. J. Org. Chem. 2012, 77, 11027
29. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009
30. Gao, F.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10961
31. Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731
32. Kawaguchi, S-i.; Ogawa, A. Org. Lett. 2010, 12, 1893
33. Uehling, M. R.; Rucker, R. P.; Lalic, G. J. Am. Chem. Soc. 2014, 136, 8799
34. Spaggiari, A.; Vaccari, D.; Davoli, P.; Torre, G.; Prati, F. J. Org. Chem. 2007, 72, 2216
35. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408
36. Mori, H.; Tsuneda Chem. Pharm. Bull. 1963, 11, 1413
37. Pross, A.; S. Sternhell, K. Aust. J. Chem. 1971, 24, 1437
38. Takeda, T.; Sasaki, R.; Nakamura, A. S.; Yamauchi, T.; Fujiwara, T. Synlett 1996, 273
39. Takeda, T.; Sasaki, R.; Yamauchi, S.; Fujiwara, T. Tetrahedron 1997, 53, 557
40. Paquette, L. A. Acc. Chem. Res. 1968, 1, 209
41. Quintard, A.; Alexakis, A. Org. Biomol. Chem. 2011, 9, 1407
42. DeSales, J.; Greenhouse, R. J. Org. Chem. 1982, 47, 3668
43. Feng, X.; Wang, J.; Zhang, J.; Yang, J.; Wang, N.; Yu, X. Org. Lett. 2010, 12, 4408
44. Fernández, M.; Uria, U.; Orbe, L.; Vicario, J. L.; Reyes, E.; Carrillo, L. J. Org. Chem. 2014, 79, 441
45. Kisselev, A. F.; van der Linden, W. A.; Overkleeft, H. S. Chem. Biol. 2012, 19, 99
46. Xi, Y.; Dong, B.; McClain, E. J.; Wang, Q.; Gregg, T. L.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Angew. Chem., Int. Ed. 2014, 53, 4657
47. Nair, V.; Augustine, A.; Suja, T. D. Synthesis 2002, 2259
48. Xu, W. M.; Tang, E.; Huang, X. Synthesis 2004, 2094
49. Dez, D.; Garca, P.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Broughton, H. B.; Urones, J. G. Tetrahedron 2005, 61, 699
50. Guan, Z.-H.; Zuo, W.; Zhao, L.-B.; Ren, Z.-H.; Liang, Y.-M. Synthesis 2007, 1465
51. Signore, G.; Malanga, C.; Menicagli, R. Tetrahedron 2008, 64, 11218
52. Das, B.; Lingaiah, M.; Damodar, K.; Bhunia, N. Synthesis 2011, 2941
53. Liang, S.; Zhang, R.-Y.; Wang, G.; Chen, S.-Y.; Yu, X.-Q. Eur. J. Org. Chem. 2013, 7050
54. Taniguchi, N. Tetrahedron 2014, 70, 1984
55. See the Supporting Information for the proposed reaction mechanism of 1,2-migration of the sulfone moiety (see SI-Scheme 8, Supporting Information).
56. Collins, K. D.; Glorius, F. Nat. Chem. 2013, 5, 597
57. See the Supporting Information for the mixed experiment and proposed reaction mechanism. We are thankful to anonymous referees for useful suggestions.