Highly Chemoselective Hydrogenation with Retention of the Epoxide Function Using a Heterogeneous Pd/C-Ethylenediamine Catalyst and THF
✍ Scribed by Hironao Sajiki; Kazuyuki Hattori; Kosaku Hirota
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 147 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
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.