Categories: C=O Bond Formation >
Synthesis of esters
Name Reactions
Recent Literature
N-Heterocyclic carbenes catalyze the oxidation of various allylic, propargylic,
and benzylic alcohols to esters with manganese(IV) oxide in excellent yields.
Saturated esters can also be accessed from aldehydes using this method. A
desymmetration of meso-1,2-diols using a chiral catalyst is described.
B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Org. Lett., 2007,
9, 371-374.
Oxidative methyl esterification of primary alcohols and diols with methanol in
the presence of acetone as a hydrogen acceptor was successfully achieved under
catalysis of an iridium complex combined with 2-(methylamino)ethanol (MAE).
N. Yamamoto, Y. Obora, Y. Ishii, J. Org. Chem., 2011,
76, 2937-2941.
Alcohols and aldehydes can be oxidized to the corresponding methyl esters by
reaction with methanol in the presence of crotononitrile as a hydrogen acceptor
using a catalyst combination of Ru(PPh3)3(CO)H2
with xantphos.
N. A. Owston, T. D. Nixon, A. J. Parker, M. K. Whittlesey, J. M. J. Williams,
Synthesis, 2009, 1459-1462.
An efficient oxidation of various acetals, including open-chain acetals,
1,3-dioxanes and 1,3-dioxalanes, with molecular oxygen in the presence of
catalytic amounts of N-hydroxyphthalimide (NHPI) and Co(OAc)2
as co-catalyst gave esters.
B. Karimi, J. Rajabi, Synthesis, 2003, 2373-2377.
In the presence of hydrogen peroxide and trimethylsilyl chloride, thiocarbonyls
desulfurize to the corresponding carbonyls in short reaction times with no side
reactions and excellent selectivity. This process is a safe, operationally
simple, and environmentally benign alternative for the desulfurization of
thiocarbonyls.
K. Bahrami, M. M. Khodaei, M. Tajik, Synthesis, 2010,
4282-4286.
The oxidation of malononitrile derivatives with peracid in methanol proceeds
with loss of the cyano groups to yield methyl esters in high yield. The method
was applied to a variety of malononitrile derivatives, some of which were
prepared by Pd- or Ir-catalyzed asymmetric allylic substitution.
S. Förster, O. Tverskoy, G. Helmchen, Synlett, 2008,
2803-2806.
An efficient oxidation of cyclic acetals provided hydroxy alkyl esters in good
yields in the presence of MCPBA.
J. Y. Kim, H. Rhee, M. Kim, J. Korean Chem. Soc., 2002, 46,
479-483.
