Categories: C-O Bond Formation > Synthesis of esters > Esterification, Transesterification, Acylation >

Transesterifications

Recent Literature

A catalytic transesterification is promoted by a tetranuclear zinc cluster. The mild reaction conditions enabled the reactions of various functionalized substrates to proceed in very good yield. A large-scale reaction under solvent-free conditions offers high environmental and economical advantages.
T. Iwasaki, Y. Maegawa, Y. Hayashi, T. Ohshima, K. Mashima, J. Org. Chem., 2008, 73, 5147-5150.

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.

K. V. N. S. Srinivas, I. Mahender, B. Das, Synthesis, 2003, 2390-2394.

Sc(OTf)₃ catalyses a direct transesterification of carboxylic esters in boiling alcohols. Methyl, ethyl, isopropyl, and allyl esters were prepared from various substrates in high yields. The application of microwave irradiation led to significantly reduced reaction times.
N. Remme, K. Koschek, C. Schneider, Synlett, 2007, 491-493.

A mild, functional group tolerant palladium-catalyzed carbonylation of aryl chlorides using atmospheric pressure of carbon monoxide allows the preparation of phenyl esters, alkyl esters and carboxylic acids. Phenyl esters are shown to be useful acylating agents, delivering libraries of carbonyl derivatives, including alkyl, allyl and thioesters, under very mild conditions.
D. A. Watson, X. Fan, S. L. Buchwald, J. Org. Chem., 2008, 73, 7096-7101.

Various alcohols, amines and N-hydroxylamines gave corresponding formylated adducts in high yields by treatment with 2,2,2-trifluoroethyl formate (TFEF). Chemoselective formylation of a primary amine could be readily achieved in the presence of an unprotected primary alcohol.
D. R. Hill, C.-N. Hsiao, R. Kurukulasuriya, S. Wittenberger, Org. Lett., 2002, 4, 111-113.

Transesterification/acylation reactions of secondary alcohols are efficiently catalyzed by N-Heterocyclic carbenes (NHC) at room temperature.
R. Singh, R. M. Kissling, M.-A. Letellier, S. P. Nolan, J. Org. Chem., 2004, 69, 209-212.

Iodine catalyses a facile transesterification of β-ketoesters.
S. P. Chavan, R. R. Kale, K. Shivasankar, S. I. Chandake, S. B. Benjamin, Synthesis, 2003, 2695-2698.