Categories: C-O Bond Formation > Synthesis of esters >
Oxidative Esterification
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Recent Literature
A simple, efficient, and high-yield procedure for the oxidative conversion of
alcohols to various types of esters and ketones was successfully carried out
with molecular iodine as the oxidant and potassium carbonate.
N. Mori, H. Togo, Tetrahedron, 2005,
61, 5915-5925.
Highly efficient, mild, and simple protocols allow the oxidation of aldehydes to
carboxylic acids and esters utilizing Oxone as the sole oxidant. These reactions
may prove to be valuable alternatives to traditional metal-mediated oxidations.
B. R. Travis, M. Sivakumar, G. O. Hollist, B. Borhan, Org. Lett., 2003,
5, 1031-1034.
Aldehydes and siloxanes form methyl esters in a single step through mild
oxidative esterification in the presence of a palladium catalyst or,
alternatively, afford secondary alcohols via TBAF-promoted arylation in the
absence of a catalyst at increased temperatures.
R. Lerebours, C. Wolf, J. Am. Chem. Soc., 2006,
128, 13052-13053.
Aldehydes undergo oxidative transformation to the methyl esters in methanol
as solvent upon treatment with catalytic amounts of vanadium pentoxide in
combination with hydrogen peroxide. This method features mild reaction conditions,
short reaction times, high efficiencies, cost-effectiveness, and facile
isolation of the desired products.
R. Gopinath, B. Patel, Org. Lett., 2000, 2, 577-579.
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.
