Categories: C-O Bond Formation > Synthesis of esters > Esterification, Transesterification, Acylation >
Esterifications
Name Reactions
Recent Literature

Borane-tetrahydrofuran complex or borane-methyl sulfide complex is used to
generate triacyloxyboranes, which can be effectively reacted with various
nucleophiles (alkylamines, arylamines, hydrazides, alcohols, phenols) at reflux
in toluene to provide the corresponding amides and esters in excellent yield.
Z. Huang, J. R. Reilly, R. N. Buckle, Synlett, 2007,
1026-1030.

Silica chloride is an efficient catalyst for esterification of carboxylic
acids with alcohols as well as for transesterification of esters by both
alcoholysis and acidolysis.
K. V. N. S. Srinivas, I. Mahender, B. Das, Synthesis, 2003, 2390-2394.

Cobalt(II) chloride hexahydrate efficiently catalyzes the acetylation of
alcohols with AcOH in high yields without the need to remove water. This
protocol is also effective with other carboxylic acids. The catalyst can be
recycled.
S. Velusamy, S. Borpuzari, T. Punniyamurthy, Tetrahedron, 2005,
61, 2011-2015.

A new facile method for selective monoesterification of diols - in
particular oligoethylene glycols - has been developed. The reaction of diols
with aromatic and aliphatic acids in presence of Al2O3
and MeSO3H gave monoesterified products in excellent yields
without use of any solvents.
H. Sharghi, M. Hosseini Sarvari, Tetrahedron, 2003, 59,
3627-3633.

A convenient procedure allows the synthesis of esters and thioesters from the
corresponding carboxylic acid using TFFH as the coupling reagent. The
preparation of N-acyl-dithiocarbamates from carboxylic acids and
1,3-thiazolidine-2-thione is also described.
M. Pittelkow, F. S. Kamounah, U. Boas, B. Pedersen, J. B. Christensen, Synthesis,
2004, 2485-2492.

The data of a study on mixed aliphatic-aromatic anhydrides suggest that
during the Yamaguchi esterification reaction, a symmetric aliphatic
anhydride is produced in situ, which upon reaction with an alcohol yields
the ester. A one-pot procedure for the regioselective synthesis of aliphatic
esters is described using benzoyl or p-toluoyl chloride instead of
the sterically hindered Yamaguchi acid chloride.
I. Dhimitruka, J. SantaLucia, Org. Lett.,
2006, 8, 47-50.
