Synthesis of esters

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Name Reactions

Reactions

Decarboxylative Esterification

Recent Literature

Nucleophilic fluorination using CsF or alkali metal fluorides was completed in short reaction time in the presence of [bmim][BF₄] affording the desired products without any byproducts. Facile nucleophilic substitutions such as halogenations, acetoxylation, nitrilation, and alkoxylations in the presence of ionic liquids provided the desired products in good yields.
D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2003, 68, 4281-4285.

A mild and efficient intermolecular addition of phenols and carboxylic acids to olefins is catalyzed by Ph₃PAuOTf.
C.-G. Yang, C. He, J. Am. Chem. Soc., 2005, 127, 6966-6967.

A rhodium-catalyzed N-H and O-H insertion of amides and carboxylic acids with α-diazo-β-ketoesters gives different α-amido- and α-carboxylic-β-ketoesters in good yields. The reactions were performed under mild conditions with 1 mol% of catalyst.
S. Bertelsen, M. Nielsen, S. Bachmann, K. A. Jorgensen, Synthesis, 2005, 2234-2238.

"Activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo compounds at -78°C. Under optimized conditions, simple vacuum filtration provides solutions of pure diazo compounds from which stable diazo species can be isolated in high yield, or that can be directly used in subsequent reactions.
M. I. Javed, M. Brewer, Org. Lett., 2007, 9, 1789-1792.

0.01 mol-% Zinc(II) salts catalyze the reaction between acetals and acid halides to provide haloalkyl ethers in near-quantitative yield in 1 - 4 h. The solutions of haloalkyl ethers can be utilized directly in reactions in which the presence of the ester byproduct does not interfere. Excess carcinogenic haloalkyl ether is destroyed on workup.
M. A. Berliner, K. Belecki, J. Org. Chem., 2005, 70, 9618-9621.

An efficient, mild and transition-metal-free N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by using various o-silylaryl triflates in the presence of CsF.
Z. Liu, R. C. Larock, J. Org. Chem., 2006, 71, 3198-3209.

A gold(I)-catalyzed rearrangement of diversely substituted allenyl carbinol esters allows the efficient, rapid, and stereoselective synthesis of various functionalized 1,3-butadien-2-ol esters via a new 1,3-shift of an ester moiety onto a gold-activated allene.
A. K. Buzas, F. M. Istrate, F. Gagosz, Org. Lett., 2007, 9, 985-988.

The preparation of diverse β-chloroethers, β-chloroacetates, and chlorohydrins is efficiently achieved under mild conditions by reaction of alkenes with trichloroisocyanuric acid in alcohols, acetic acid or aqueous acetone, respectively.
G. Fonseca Mendonça, A. Manzolillo Sanseverino, M. C. S. de Mattos, Synthesis, 2003, 45-48.

A new palladium-catalyzed method allows the oxygenation of unactivated sp³ C-H bonds of a wide variety of alkane substrates containing readily available oxime and/or pyridine directing groups with extremely high levels of chemo-, regio-, and in some cases diastereoselectivity.
L. V. Desai, K. L . Hull, M. S. Sanford, J. Am. Chem. Soc., 2004, 126, 9542-9543.