Regioselective lateral or vinyl C-H lithiation/1,5-retro-Brook rearrangement via quinolyl or pyridyl ring directed deprotonation

Tetrahedron

Volumn 69, Issue 26, 2013, Pages 5545-5549

  He, Yongping ^a   Ma, Bin ^a   Yang, Juan ^a   Xie, Xingang ^a   She, Xuegong ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Benzyl silanes; Directed deprotonation; Lateral lithiation; Vinyl lithiation 1,5 Retro Brook rearrangement; Vinyl silanes

Indexed keywords

CARBON; HYDROGEN; SILANE;

ARTICLE; LITHIATION; METALLATION; PRIORITY JOURNAL;

EID: 84878222035     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.065     Document Type: Article

References (43)

1. T. Sakakura, Y. Tokunaga, T. Sodeyama, and M. Tnanka Chem. Lett. 1987 2375 2378
2. Y. Uchimaru, and M. Tanaka Organometallics 12 1993 2065 2069
3. K. Ezbiansky, D.J. Sining, R. Zayes, and D.H. Berry Organometallics 17 1998 1455 1457
4. F. Kakiuchi, and M. Matsumoto J. Organomet. Chem. 686 2003 134 144
5. F. Kakiuchi, and K. Tsuchiya J. Am. Chem. Soc. 126 2004 12792 12793
6. S. Rendler, and M. Oestreich J. Am. Chem. Soc. 129 2007 502 503
7. E.M. Simmons, and J.F. Hartwig J. Am. Chem. Soc. 132 2010 17092 17095
8. H.F.T. Klare, M. Oestreich, J. Ito, H. Nishiyama, Y. Ohki, and K. Tatsumi J. Am. Chem. Soc. 133 2011 3312 3315
9. T. Mita, K. Michigami, and Y. Sato Org. Lett. 14 2012 3462 3465
10. Baran Group Meeting Directed Metallation: A Survival Guide
11. M.C. Whisler, V. Snieckus, and P. Beak Angew. Chem., Int. Ed. 43 2004 2206 2225 and references cited therein
12. Y. He, X. Xie, and X. She Tetrahedron 69 2012 559 563 For other 1,4-retro-Brook rearrangements, see
13. E. Winter, and R. BrJckner Synlett 1994 1049 1053
14. X.-L. Jiang, and W.F. Bailey Organometallics 14 1995 5704 5707
15. S.M.E. Simpkins, B.M. Kariuki, C.S. Arico, and L.R. Cox Org. Lett. 5 2003 3971 3974
16. M.R. Nahm, and J.S. Johnson Angew. Chem., Int. Ed. 44 2005 2377 2379
17. S. Yamago, K. Fujita, M. Miyoshi, M. Kotani, and J. Yoshida Org. Lett. 7 2005 909 911
18. A. Nakazaki, T. Nakai, and K. Tomooka Angew. Chem., Int. Ed. 45 2006 2235 2238
19. H. Mori, T. Matsuo, Y. Yoshioka, and S. Katsumura J. Org. Chem. 71 2006 9004 9012
20. Y. Mori, Y. Futamura, and K. Horisaki Angew. Chem., Int. Ed. 47 2008 1091 1093
21. Clayden, G. In Organolithiums: Selectivity for Synthesis; Baldwin, J. E.; Williams, R. M., Eds.; Tetrahedron Organic Chemistry Series; Vol. 23, Chapter 2, pp 28-36.
22. G. Anderson, D.W. Cameron, G.I. Feutrill, and R.W. Read Tetrahedron Lett. 22 1981 4347 4348
23. J. Clayden, D.W. Watson, and M. Chambers Tetrahedron 61 2005 3195 3203
24. J. Kristensen, and P. Vedsø Org. Lett. 3 2001 1435 1437
25. S. Florio, V. Capriati, V. Aggarwa, and A. Salomone Org. Lett. 6 2004 4191 4194
26. M. Mofi, and G. Vassilikogannakis Org. Lett. 7 2005 3347 3350
27. V. Capriati, and S. Florio Org. Lett. 7 2005 3749 3752
28. R.E. Mulvey, and F. Mongin Angew. Chem., Int. Ed. 46 2007 3802 3824
29. Y. Sang, and H. Zhai J. Org. Chem. 73 2008 3589 3592
30. F. Affortunato, S. Florio, and R. Luisi J. Org. Chem. 73 2008 9214 9220
31. C. James, and V. Snieckus J. Org. Chem. 74 2009 4094 4103
32. M.A. Reed, M.T. Chang, and V. Snieckus Org. Lett. 6 2004 2297 2300
33. J. Cotter, and D.F. O'Shea Org. Lett. 9 2007 1493 1496
34. T. Tricotet, and D.F. O'Shea J. Am. Chem. Soc. 131 2009 3142 3143
35. C.H. Borning, and F.W. Burgstrom J. Am. Chem. Soc. 67 1945 2110 2111
36. R. Budugu, and C.D. Geddes J. Am. Chem. Soc. 127 2005 3635 3641
37. M.C. Basheer, and S. Das Tetrahedron 63 2007 1617 1623
38. A. Okamoto Tetrahedron 63 2007 3465 3470
39. X. Wang, X. Li, and C.A. Schalley Org. Biomol. Chem. 8 2010 1017 1026
40. S.H. Mashraqui Tetrahedron Lett. 51 2010 1306 1308
41. S. Sen, and P. Chattopadhyay Analyst 137 2012 3975 3981
42. S.K. Shahoo, D. Sharma, R.K. Bera, and J.F. Callan Chem. Soc. Rev. 41 2012 7195 7227
43. N. Karton-Lifshin, L. Albertazzi, M. Bentikov, P.S. Baran, and D. Shabat J. Am. Chem. Soc. 134 2012 20412 20420