Categories: C-O Bond Formation >
Synthesis of anhydrides
Name Reactions
Recent Literature
The reaction between carboxylic acids and dialkyl dicarbonates, in the presence
of a weak Lewis acid such as magnesium chloride and the corresponding alcohol as
the solvent, leads to esters in excellent yields. The mechanism involves a
double addition of the acid to the dicarbonate, affording a carboxylic anhydride
and CO2.
G. Bartoli, M. Bosco, A. Carlone, R. Dalpozzo, E. Marcantoni, P. Melchiorre, L.
Sambri, Synthesis, 2007,
3489-3496.
A light-mediated, Cu-catalyzed process provides aliphatic, symmetric acid
anhydrides directly by carbonylation of alkyl (pseudo)halides in a single step
without any precious metal additives. The transformation requires only simple Cu
salts and abundant bases to generate an efficient heterogeneous Cu0
photocatalyst in situ.
P. Tung, N. P. Mankad, J. Am. Chem. Soc.,
2023, 145, 9423-9427.
N-Benzoylsaccharins and N-Boc-protected benzamides reacted with H2O
in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 25 °C to produce the
corresponding symmetrical anhydrides in high yields through C-N bond cleavage.
In addition, N-benzoylsaccharins reacted with benzoic acid derivatives to
generate unsymmetrical anhydrides in high yields.
I. A. Bashir, S. Lee, J. Org. Chem., 2023, 88,
6159-6167.
N-Benzoylsaccharins and N-Boc-protected benzamides reacted with H2O
in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 25 °C to produce the
corresponding symmetrical anhydrides in high yields through C-N bond cleavage.
In addition, N-benzoylsaccharins reacted with benzoic acid derivatives to
generate unsymmetrical anhydrides in high yields.
I. A. Bashir, S. Lee, J. Org. Chem., 2023, 88,
6159-6167.