TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group

Synlett

Volumn , Issue 18, 2010, Pages 2717-2720

  Kutsumura, Noriki ^a   Kubokawa, Keisuke ^a   Saito, Takao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

2 bromoalk 1 enes; alkynes; elimination; TBAF; vicinal dibromides

Indexed keywords

1 BROMOALK 1 ENE DERIVATIVE; 1,2 DIBROMOALKANE DERIVATIVE; 2 BROMOALK 1 ENE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BROMINE DERIVATIVE; DIBROMIDE DERIVATIVE; OXYGEN; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; DEHYDROBROMINATION; ELIMINATION REACTION; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 78149285430     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258813     Document Type: Article

References (40)

1. Paqutte L A., Hofferberth J E., J. Org. Chem. 2003 68 2266
2. Poss C S., Rychnovsky S D., Schreiber S L., [nl]J. Am. Chem. Soc. 1993 115 3360
3. Yokota M, Toyota M, Ihara M, Chem. Commun. 2003 422
4. Novikov Y Y., Sampson P, J. Org. Chem. 2005 70 10247
5. Vanbrunt M P., Ambenge R O., Weinreb S M., J. Org. Chem. 2003 68 3323
6. Suzuki H, Sakai N, Iwahara R, Fujiwara T, Satoh M, Kakehi A, Konakahara T, J. Org. Chem. 2007 72 5878
7. Miyamoto H, Okawa Y, Nakazaki A, Kobayashi S, Tetrahedron Lett. 2007 48 1805
8. Ohno H, Yamamoto M, Iuchi M, Tanaka T, Angew. Chem. Int. Ed. 2005 44 5103
9. Prusov E, Röhm H, Maier M E., Org. Lett. 2006 8 1025
10. Daniel P T., Koert U, Schuppan J, Angew. Chem. Int. Ed. 2006 45 872
11. Denmark S E., Yang S M., J. Am. Chem. Soc. 2004 126 12432
12. Fujii K, Maki K, Kanai M, Shibasaki M, Org. Lett. 2003 5 733
13. Chavez D E., Jacobsen E N., Angew. Chem. Int. Ed. 2001 40 3667
14. Duffault J M., Einhorn J, Alexakis A, Tetrahedron Lett. 1991 32 3701
15. Sugiyama H, Yokokawa F, Shioiri T, Org. Lett. 2000 2 2149
16. Kamiya N, Chikami Y, Ishii Y, Synlett 1990 675
17. Narayan R S., Borhan B, J. Org. Chem. 2006 71 1416
18. Usugi S, Yorimitsu H, Shinokubo H, Oshima K, Bull. Chem. Soc. Jpn. 2002 75 2687
19. Izzo I, De Caro S, De Riccardis F, Spinella A, Tetrahedron Lett. 2000 41 3975
20. Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett. 1975 16 4467
21. Ireland R E., Wipf P, J. Org. Chem. 1990 55 1425
22. Ohgiya T, Nakamura K, Nishiyama S, Bull. Chem. Soc. Jpn. 2005 78 1549
23. Ohgiya T, Nishiyama S, Chem. Lett. 2004 33 1084
24. Ohgiya T, Nishiyama S, Heterocycles 2004 63 2349
25. Ohgiya T, Nishiyama S, Tetrahedron Lett. 2004 45 8273
26. Yokoyama T, Kutsumura N, Ohgiya T, Nishiyama S, Bull. Chem. Soc. Jpn. 2007 80 578
27. Kutsumura N, Yokoyama T, Ohgiya T, Nishiyama S, Tetrahedron Lett. 2006 47 4133
28. Ohgiya T, Kutsumura N, Nishiyama S, Synlett 2008 3091
29. Ohgiya T, Kutsumura N, Nishiyama S, J. Synth. Org. Chem. Jpn. 2008 66 139
30. Kutsumura N, Niwa K, Saito T, Org. Lett. 2010 12 3316
31. Andrei D, Wnuk S F., Org. Lett. 2006 8 5093
32. Nakata M, Enari H, Kinoshita M, Bull. Chem. Soc. Jpn. 1982 55 3283
33. Okutani M, Mori Y, J. Org. Chem. 2009 74 442
34. Okutani M, Mori Y, Tetrahedron Lett. 2007 48 6856
35. Feng L, Kumar D, Birney D M., Kerwin S M., Org. Lett. 2004 6 2059
36. MatloubiMoghaddam F, Emami R, Synth. Commun. 1997 27 4073
37. Fürstner A, DeSouza D, Parra-Rapado L, Jensen J T., Angew. Chem. Int. Ed. 2003 42 5358
38. Kim D, Lee J, Shim P J., Lim J I., Doi T, Kim S, J. Org. Chem. 2002 67 772
39. Yoshimitsu T, Ogasawara K, J. Chem. Soc., Chem. Commun. 1994 2197
40. Keusenkothen P F., Smith M B., J. Chem. Soc., Perkin Trans. 1 1994 2485