Categories: C-O Bond Formation > Synthesis of esters > Esterification, Transesterification, Acylation >
Acylations
Name Reactions
Recent Literature
Acylation of alcohols, thiols, and sugars were studied with a variety of
Lewis acids, and it was found that Cu(OTf)2 was very efficient in
catalyzing the reaction under mild conditions in CH2Cl2.
K. L. Chandra, P. Saravan, R. K. Singh, V. K. Singh, Tetrahedron, 2002, 58,
1369-1374.
Copper(II) tetrafluoroborate efficiently catalyzes acetylation of
structurally diverse phenols, alcohols, thiols, and amines with
stoichiometric amounts of Ac2O under solvent-free conditions at
room temperature. Acid-sensitive alcohols are smoothly acetylated without
competitive side reactions.
A. K. Chakraborti, R. Gulhane, Shivani, Synthesis, 2004,
111-115.
Various alcohols, phenols, amines and thiols
may easily be converted into acetate derivatives by treatment
with acetic anhydride in the presence of
acetonyltriphenylphosphonium bromide in good yields at room
temperature. With the same precatalyst, both aliphatic and aromatic aldehydes
can be transformed into the corresponding gem-diacetates under reflux
conditions.
A. T. Khan, L. H. Choudry, S. Ghosh, Eur. J. Org. Chem., 2005,
2782-2787.
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.
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.
M. Bassetti, A. D'Annibale, A. Fanfoni, F. Minissi, Org. Lett., 2005, 7, 1805-1808.
Er(OTf)3 is an efficient Lewis acid catalyst in a mild
deprotection of benzylidene derivatives. A simultaneous cleavage of
benzylidene acetals and peracetylation of the substrates is obtained in
quantitative yields in acetic anhydride as solvent.
A. Procopio, R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, G. Romeo, Org. Biomol. Chem., 2005, 3, 4129-4133.
