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48.1.3.6.1.1.4.5.7 Variation 7: Selective Hydrogenation in the Presence of a Cyano Group

DOI: 10.1055/sos-SD-048-00166

Chessum, N.; Couty, S.; Jones, K.Science of Synthesis, (200948322.

Nitriles and especially aryl nitriles are known to be reduced under classical heterogeneous conditions. However, selectivity for alkene reduction can be poor, and reduction of benzonitrile in the presence of palladium on carbon affords a mixture of benzylamine and dibenzylamine.[‌168‌] Similarly, hydrogenation of cyclohexene-1-carbonitrile (92) with platinum(IV) oxide results in a mixture of cyclohexanecarbonitrile (93) (31% yield) and bis(cyclohexylmethyl)amine (94) (Scheme 43).[‌169‌] However, aryl nitriles have been shown to survive when performing reduction with a catalytic amount of palladium on carbon poisoned with ethylenediamine [Pd/C(en)]. Thus, 4-butylbenzonitrile (96) is obtained from 4-(but-3-enyl)benzonitrile (95) in 84% yield (Scheme 43).[‌168‌]

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