Cleavage of benzyl ethers by triphenylphosphine hydrobromide

Tetrahedron Letters

Volumn 51, Issue 47, 2010, Pages 6143-6145

  Ramanathan, Mani ^a   Hou, Duen Ren ^a  

^a NATIONAL CENTRAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; BENZYL DERIVATIVE; BROMIDE; ETHER; PHOSPHONIUM DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; DEBENZYLATION; DEPROTECTION REACTION; OXIDATION REDUCTION REACTION; STOICHIOMETRY;

EID: 77958461204     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.065     Document Type: Article

References (43)

1. P.G.M. Wuts, and T.W. Greene Protective Groups in Organic Synthesis 4th edition 2007 John Wiley & Sons New York 102
2. S.A. Weissman, and D. Zewge Tetrahedron 61 2005 7833
3. K. Jarowicki, and P. Kocienski J. Chem. Soc., Perkin Trans. 1 2001 2109, and references cited therein
4. A. Vincent, and J. Prunet Tetrahedron Lett. 47 2006 4075
5. O. Kanie, G. Grotenbreg, and C.H. Wong Angew. Chem., Int. Ed. 39 2000 4545
6. T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, and S. Terashima Tetrahedron 53 1997 10239
7. K. Horita, T. Yoshioka, T. Tanaka, Y. Oikawa, and O. Yonemitsu Tetrahedron 42 1986 3021
8. Y. Oikawa, T. Tanaka, K. Horita, and O. Yonemitsu Tetrahedron Lett. 25 1984 5397
9. Reductive cleavage: E. Alonso, D.J. Ramón, and M. Yus Tetrahedron 53 1997 14355
10. H.-J. Liu, J. Yip, and K.S. Shia Tetrahedron Lett. 38 1997 2252
11. I. Schön Chem. Rev. 84 1984 287
12. Oxidative cleavage: N. Ikemoto, and S.L. Schreiber J. Am. Chem. Soc. 114 1992 2524
13. S. Baek, H. Jo, H. Kim, S. Kim, and D. Kim Org. Lett. 7 2005 75
14. Other debenzylation: J.R. Hwu, F.-F. Wong, J.-J. Huang, and S.-C. Tsay J. Org. Chem. 62 1997 4097
15. H. Yajima, N. Fuji, H. Ogawa, and H. Kawatani J. Chem. Soc., Chem. Commun. 1974 107
16. S. Fletcher, and P.T. Gunning Tetrahedron Lett. 49 2008 4817
17. T. Petchmanee, P. Ploypradith, and S. Ruchirawat J. Org. Chem. 71 2006 2892
18. G.V.M. Sharma, C.G. Reddy, and P.R. Krishna J. Org. Chem. 68 2003 4574
19. M.E. Jung, and M.A. Lyster J. Org. Chem. 42 1977 3761
20. Y. Guindon, C. Yoakim, and H.E. Morton Tetrahedron Lett. 24 1983 2969
21. D.R. Williams, D.L. Brown, and J.W. Benbow J. Am. Chem. Soc. 111 1989 1923
22. J.D. Kim, G. Han, O.P. Zee, and Y.H. Jung Tetrahedron Lett. 44 2003 733
23. E. Rizzi, S. Dallavalle, L. Merlini, G.L. Beretta, G. Pratesib, and F. Zunino Bioorg. Med. Chem. Lett. 15 2005 4313
24. M.V. Bhatt, and S.U. Kulkarni Synthesis 1983 249
25. M. Tiecco Synthesis 1988 749
26. D.A. Evans, and J.R. Scheerer Angew. Chem., Int. Ed. 44 2005 6038
27. Z. Xiong, D.A. Gao, D.A. Cogan, D.R. Goldberg, M.-H. Hao, N. Moss, E. Pack, C. Pargellis, D. Skow, T. Trieselmann, B. Werneburg, and A. White Bioorg. Med. Chem. Lett. 18 2008 1994
28. S.P. Hajela, A.R. Johnson, J. Xu, C.J. Sunderland, S.M. Cohen, D.L. Caulder, and K.N. Raymond Inorg. Chem. 40 2001 3208
29. M. Kim, Q. Mao, B.L. Davidson, and D.F. Wiemer J. Med. Chem. 46 2003 1603
30. P. Leighton, and J.K.M. Sanders J. Chem. Soc., Perkin Trans. I 1987 2385
31. T. Messeri, G. Pentassuglia, and R. Di Fabio Tetrahedron Lett. 42 2001 3227
32. N. Cohen, G. Weber, B.L. Banner, R.J. Lopresti, B. Schaer, A. Focella, G.B. Zenchoff, A.-M. Chiu, L. Todaro, M. O'Donnel1, A.F. Welton, D. Brown, R. Garippa, H. Crowley, and D.W. Morgan J. Med. Chem. 32 1989 1842
33. M.S. Meier L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis Vol. 8 1995 John Wiley & Sons New York 5392
34. A. Hercouet, and M. Le Corre Synthesis 1988 157
35. V. Bolitt, C. Mioskowski, D.S. Shin, and J.R. Falck Tetrahedron Lett. 29 1988 4583
36. K.J. McCullough Tetrahedron Lett. 23 1982 2223
37. Standard procedure for debenzylation, condition A: A solution of a benzyl ether (0.5 mmol), triphenylphosphine hydrobromide (0.55 mmol) in dry acetonitrile (0.5 mL) was placed in a vial (10 mL, for microwave reaction). The vial was capped and heated to 100 °C for 30 min in a microwave oven (CEM Discover). After cooling to room temperature, the suspension was diluted with EtOAc (10 mL), and filtered to remove the benzyltriphenylphosphonium bromide salt. The organic layer was concentrated under reduced pressure to give the desired product. The crude product could be further purified by flash column chromatography. Condition B: A solution of an alkyl benzyl ether or aryl benzyl ether (0.5 mmol) in dry acetonitrile (1 mL) was added with triphenylphosphine hydrobromide (0.55 mmol). The reaction mixture was heated to reflux for 12 h. The work-up procedure was the same as the microwave-assisted condition.
38. 4, filtered, and concentrated. The crude product was further purified by flash column chromatography (20%, EA/hexanes) to give 36 (34 mg, 0.26 mmol, 57%).
39. M.B. Smith, and J. March March's Advanced Organic Chemistry 2007 Wiley-Interscience New York 244
40. This deprotection is another example of 'push-pull' mechanism: K. Fuji, K. Ichikawa, M. Node, and E. Fujita J. Org. Chem. 44 1979 1661
41. Y. Kiso, K. Ukawa, S. Nakamura, K. Ito, and T. Akita Chem. Pharm. Bull. Jpn. 28 1980 673
42. H. Yajima, and N. Fujii J. Am. Chem. Soc. 103 1981 5867
43. J.P. Tam, W.F. Heath, and R.B. Merrifield J. Am. Chem. Soc. 108 1986 5242 A reviewer's comment is appreciated