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Synthesis of anhydrides

Name Reactions


Yamaguchi Esterification


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.