Unexpected deprotection of silyl and THP ethers induced by serious disparity in the quality of Pd/C catalysts and elucidation of the mechanism

Tetrahedron

Volumn 60, Issue 29, 2004, Pages 6189-6195

  Ikawa, Takashi ^a   Sajiki, Hironao ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Acidity; Hydrogenation; Palladium on carbon; Silyl ether

Indexed keywords

CHLORIDE; HYDROGEN; PALLADIUM; SILANE DERIVATIVE; TETRAHYDROPYRANYL ETHER;

ARTICLE; CATALYSIS; CATALYST; DEGRADATION; DEPROTECTION REACTION; HYDROGENATION; MOLECULAR MECHANICS; PRIORITY JOURNAL; PUBLISHING; SOLVOLYSIS;

EID: 3042662232     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.040     Document Type: Article

References (28)

1. Selected reviews: (a) Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;Wiley-Interscience, New York. pp 49-54 and 113-148
2. Kocienski P.J. Protecting Groups. 1994;Thieme, Stuttgart. p 28
3. Pearson A.J., Roush W.R. Handbook of Reagents for Organic Synthesis; Activating Agents and Protecting Groups. 1999;Wiley, New York. p 84
4. Deprotection of silyl ether using hydride: (a) Shekhani M.S., Khan K.M., Mahmood K. Tetrahedron Lett. 29:1988;6161-6162
5. Corey E.J., Jones G.B. J. Org. Chem. 57:1992;1028-1029
6. Deproteciton of THP ether using hydride: Cossy J., Bellosta V., Müller M.C. Tetrahedron Lett. 33:1992;5045-5046
7. Palladium-catalyzed hydrogenolysis of silyl ether: (a) Toshima K., Yanagawa K., Mukaiyama S., Tatsuta K. Tetrahedron Lett. 31:1990;6697-6698
8. Cormier J.F. Tetrahedron Lett. 32:1991;187-188
9. Cormier J.F., Isaac M.B., Chen L.-F. Tetrahedron Lett. 34:1993;243-246
10. Lee K., Wiemer D.F. J. Org. Chem. 58:1993;7808-7812
11. Wilson N.S., Keay B.A. J. Org. Chem. 61:1996;2918-2919
12. For reviews, see: (a) Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis. 2001;Wiley, New York. pp 34-38
13. Rylander P.N. Hydrogenation Methods. 1985;Academic, New York. p 10
14. Kaisalo L., Hase T.A. Tetrahedron Lett. 42:2001;7699-7701
15. Hattori K., Sajiki H., Hirota K. Tetrahedron Lett. 41:2000;5711-5714
16. Hattori K., Sajiki H., Hirota K. Tetrahedron. 57:2001;2109-2114
17. Sajiki H., Ikawa T., Hattori K., Hirota K. Chem. Commun. 2003;654-655
18. Rotulo-Sims D., Prunet J. Org. Lett. 4:2002;4701-4704
19. Sajiki H., Ikawa T., Hirota K. Tetrahedron Lett. 44:2003;7407-7410
20. 8
21. Maier W., Chettile S.J., Rai R.S., Thomas G. J. Am. Chem. Soc. 108:1986;2608-2616
22. a
23. 2
24. Sajiki H., Ikawa T., Yamada H., Tsubouchi K., Hirota K. Tetrahedron Lett. 44:2003;171-174
25. 2 was absolutely reduced to Pd(0) by MeOH and a very small amount of hydrogen chloride should be generated during the short reaction period
26. Roush W.R., Russo-Rodriquez S. J. Org. Chem. 52:1987;598-603
27. Bernady K.F., Floyd M.B., Poletto J.F., Weiss M.J. J. Org. Chem. 44:1979;1438-1447
28. Rücker C. Chem. Rev. 95:1995;1009-1064