Selective
hydrogenation of aromatic ketones without hydrogenation
of aromatic rings over Pd/C is very interesting but still challenging.
Herein, we report a hydrogen-bonding-mediated strategy for selective
hydrogenation of aryl ketones to either aryl alcohols or aryl alkanes
at room temperature, which is achieved over Pd/C in imidazolium-based
ionic liquids (ILs) via altering the IL anions from [Cl]− to [BF4]−. 1-Butyl-3-methyl-imidazolium
([BMIm]+) ILs with [Cl]− and [BF4]− anions show high performances, affording
a series of aromatic alcohols or alkanes with 100% selectivity and
high yields, respectively. Mechanism investigation indicates that
the π–π interaction between the ILs and the aromatic
ring of the ketones may inhibit the hydrogenation of the aromatic
ring, and the dual H-bonding interaction of the IL cation and anion
with the resultant alcohol from the ketone hydrogenation mediates
the hydrogenation selectivity. This catalytic protocol is simple,
highly efficient, and selective toward target products, which may
have promising applications.