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Ionic hydrogenation
Ionic Hydrogenation refers to hydrogenation achieved by the addition of a proton and a hydride to substrate; in contrast to traditional hydrogenation which is achieved using H2. The proton and hydride transfers can be either sequential or concerted.〔Bullock, R. M. "Ionic Hydrogenations," in The Handbook of Homogeneous Hydrogenation (eds J. G. de Vries and C. J. Elsevier), Wiley-VCH Verlag GmbH, Weinheim, Germany, 2007. 〕 Usually ionic hydrogenation is shown to occur in two steps, starting with protonation.
:R2C=Y + H+ → R2C+-YH
:R2C+-YH + "H−" → R2CH-YH
==Substrates==
Ionic hydrogenation is employed when the substrate can produce a stable carbonium ion. Polar double bonds are favored substrates. In the case of metal-catalyzed ionic hydrogenation, the substrates and their products must not bind to metal sites, as this would interfere with H2 activation. Ketones are the most common substrates. Less common are imines and N-heterocycles. The reaction can also be performed in reverse to effect hydrogenolysis. Liquid substrates can sometimes be hydrogenated without solvent, a goal of green chemistry.〔
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