Categories: C-N Bond Formation > Synthesis of amides >
Synthesis of amides by rearrangements, hydrolysis, or oxidation
Name Reactions
Recent Literature
A simple ruthenium catalyst mediates a direct coupling between an alcohol and an
amine with the liberation of two molecules of dihydrogen. The active catalyst is
generated in situ from an easily available ruthenium complex, an N-heterocyclic
carbene and a phosphine. The reaction allows primary alcohols to be coupled with
primary alkylamines to afford secondary amides in good yields.
L. U. Nordstrøm, H. Vogt, R. Madsen, J. Am. Chem. Soc., 2008,
130, 17672-17673.
An in situ generated catalyst from readily available RuH2(PPh3)4,
an N-heterocyclic carbene (NHC) precursor, NaH, and acetonitrile showed
high activity for the amide synthesis directly from either alcohols or aldehydes
with amines.
S. Muthaiah, S. C. Ghosh, J.-E. Jee, C. Chen, J. Zahng, S. H. Hong, J. Org. Chem., 2010,
75, 3002-3006.
A Cu-catalyzed oxidative amidation-diketonization reaction of terminal alkynes
leads to α-ketoamides. In this copper-catalyzed radical process, O2
not only participates as the ideal oxidant but also undergoes dioxygen
activation under ambient conditions.
C. Zhang, N. Jiao, J. Am. Chem. Soc., 2010,
132, 28-29.
A wide range of aldoximes has been converted into the corresponding amides in
high yield and selectivity using the ruthenium-based catalyst Ru(PPh3)3(CO)H2/dppe/TsOH
with catalyst loading as low as 0.04 mol%.
N. A. Owston, A. J. Parker, J. M. J. Williams, Org. Lett., 2007,
9, 3599-3601.
[Ir(Cp*)Cl2]2 catalyzes the rearrangement of oximes to
furnish amides. An iridium-catalyzed transfer
hydrogenation between alcohols and styrene and the subsequent formation of an
oxime allows the conversion of alcohols
into amides in a one-pot process.
N. A. Owston, A. J. Parker, J. M. J. Williams, Org. Lett., 2007,
9, 73-75.
