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Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C‐Ethylenediamine Catalyst and THF
Author(s) -
Sajiki Hironao,
Hattori Kazuyuki,
Hirota Kosaku
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20000616)6:12<2200::aid-chem2200>3.0.co;2-3
Subject(s) - chemoselectivity , hydrogenolysis , epoxide , ethylenediamine , chemistry , catalysis , olefin fiber , palladium , organic chemistry , solvent , azide
In general, palladium‐carbon (Pd/C) catalyzed hydrogenation of epoxides affords the corresponding primary and secondary alcohols as a mixture. It has been found that the catalytic activity of a Pd/C‐ethylenediamine complex catalyst [Pd/C(en)] in the hydrogenolysis of epoxide functions is drastically reduced. Herein we describe a mild and chemoselective method for the hydrogenation of olefin, nitro, and azide functions with retention of the epoxide function. The chemoselectivity was accomplished by using a combination of 5 % Pd/C(en) and THF as solvent. A significant drop in the chemoselectivity of the hydrogenation is observed with 5 % Pd/C(en) in MeOH. These results reinforce the utility of epoxides as important precursors of alcohols in synthetic chemistry.