A versatile, selective,
and recyclable heterogeneous catalytic
method for the methylation of C–H bonds in alcohols, ketones,
and indoles with methanol under oxidant-free conditions using a Pt-loaded
carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic
system is effective for various methylation reactions: (1) the β-methylation
of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols,
(2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a
borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation
of the alcohol(s) to afford aldehydes, which subsequently undergo
a condensation reaction with the nucleophile (aldehyde, ketone, or
indole), followed by hydrogenation of the condensation product by
Pt–H species to yield the desired product. In all of the methylation
reactions explored in this study, the Pt/C catalyst exhibits a significantly
higher turnover number than other previously reported homogeneous
catalytic systems. Moreover, it is demonstrated that the high catalytic
activity of Pt can be rationalized in terms of the adsorption energy
of hydrogen on the metal surface, as revealed by density functional
theory calculations on different metal surfaces.
ZrO 2 -supported Pt clusters;i i) the amidation of triglycerides under gaseous NH 3 catalyzed by high-silica H-beta (Hb)z eolite at 180 8C; iii)the Hb-promoted synthesis of nitrilesf rom triglycerides and gaseous NH 3 at 220 8C. These methods are widely applicable to the transformation of various triglycerides (C 4 -C 18 skeletons)i nto the corresponding amines,a mides, and nitriles.
An efficient heterogeneous Nb2O5 catalytic system has been developed for industrially important and challenging amide hydrolysis reaction to carboxylic acid through cleavage of resonance stabilized amidic C–N bond.
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