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(a) Sajiki, H. (1995) Selective Inhibition of Benzyl Ether Hydrogenolysis with Pd/C Due to the Presence of Ammonia, Pyridine or Ammonium Acetate. Tetrahedron Letters, 36, 3465-3468. http://dx.doi.org/ 10.1016/0040-4039(95)00527-J; (b) Sajiki, H., Kuno, H. and Hirota, K. (1997) Chemoselective Inhibition of the Hydrogenolysis of the MPM Protective Group for Phenolic Hydroxy Functions Using a Pd/C-Pyridine Catalyst. Tetrahedron Letters, 38, 399-402. http://dx.doi.org/10. 1016/S0040-4039(96)02309-X; (c) Saijiki, H., Kuno, H. and Hirota, K. (1998) Suppression Effect of the Pd/C-Catalyzed Hydrogenolysis of a Phenolic Benzyl Protective Group by the Addition of Nitrogen Containing Bases. Tetrahedron Letters, 39, 7127-7130. http://dx. doi.org/10.1016/S0040-4039(98)01514-7; (d) Sajiki, H. and Hirota, K. (1998) The Formation of a Novel Pd/C Catalyzed Hydrogenation Using a Catalyst Posion: Chemoselective Inhibition of the Hydrogenolysis for O-Benzyl Protective Group by the Addition of a Nitrogen-Containing Base. Tetrahedron, 54, 13981-13996. http://dx.doi.org/10.1016/S0040-4020(98)00882-5; (e) Sajiki, H. and Hirota, K. (2003) Palladium-Catalyzed Chemoselective Hydrogenation in the Presence of a Phenolic MPM Protective Group Using Pyridine as a Catalyst Poison. Chemical and Pharmaceutical Bulletin, 51, 320-324; (e) Sajiki, H., Hattori, K. and Hirota, K. (1998) The Formation of a Novel Pd/C-Ethylenediamine Complex Catalyst: Chemoselective Hydrogenation without Deprotection of the O-Benzyl and ZV-Cbz Groups. The Journal of Organic Chemistry, 63, 7990-7992.
http://dx.doi.org/10.1021/jo9814694
has been cited by the following article:
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TITLE:
Hydrogenation of Alkenes with NaBH4, CH3CO2H, Pd/C in the Presence of O- and N-Benzyl Functions
AUTHORS:
Nuha Al Soom, Thies Thiemann
KEYWORDS:
Alkene Hydrogenation, Benzyl Ether, Benzyl Ester, N-Benzyl Group
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.6 No.1,
March
4,
2016
ABSTRACT: NaBH4, CH3CO2H, Pd/C has been described as an effective reagent system to hydrogenate alkenes. Here, we show that the hydrogenation occurs chemoselectively, making it possible to hydrogenate alkenes under Pd/C catalysis with hydrogen created in situ without O- or N-debenzylation.
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