Categories: C-O Bond Formation >
Synthesis of esters
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Name Reactions
Reactions
Decarboxylative Esterification
Recent Literature
A very fast, microwave-assisted formation of carboxylic esters via reaction of carboxylic acids with O-alkylisoureas
derived from primary and secondary alcohols proceeds in good yields with clean inversion of configuration where appropriate.
The reaction works well with very hindered carboxylic acids.
A. Chighine, S. Crosignani, M.-C. Arnal, M. Bradley, B. Linclau, J. Org. Chem., 2009,
74, 4638-4641.
A. Chighine, S. Crosignani, M.-C. Arnal, M. Bradley, B. Linclau, J. Org. Chem., 2009,
74, 4638-4641.
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.
The presence of a base stronly improves the efficiency and the selectivity of
the Pd-catalyzed oxidation of terminal alkenes in carboxylic acids. The
methodology is particularly well adapted for the oxidation of homoallylic
alcohols, for which the resulting acyloxylated products are obtained selectively
as E-isomers in good yields.
E. Thiery, C. Aouf, J. Belloy, D. Harakat, J. Le Bras, J. Muzart, J. Org. Chem., 2010,
75, 1771-1774.
A method for the preparation of a wide range of branched allylic esters from
terminal alkynes proceeds via a redox-neutral propargylic CH activation
employing a rhodium(I)/DPEphos catalyst.
A. Lumbroso, P. Koschker, N. R. Vautravers, B. Breit, J. Am. Chem. Soc., 2011,
133, 2386-2389.
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.
A Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids with
arylboronic acids is a facile and practical methodology to access phenolic
esters in good yields. The procedure tolerates various functional groups, such
as methoxycarbonyl, acetoxy, free phenolic hydroxyl, vinyl, nitro,
trifluoromethyl, methoxyl, bromo, chloro, iodo, and acetyl groups.
L. Zhang, G. Zhang, M. Zhang, J. Cheng, J. Org. Chem., 2010,
75, 7472-7474.
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.
Various anilides have been directly ortho-acetoxylated with acetic acid as the acetate
source and K2S2O8 as the oxidant in the
presence of
Pd(OAc)2 as catalyst. The amide group is an elegant directing group to convert aromatic sp2 C-H bonds into C-O bonds.
G.-W. Wang, T.-T. Yuan, X.-L. Wu, J. Org. Chem., 2008,
73, 4717-4720.
A rhodium-catalyzed, selective intermolecular anti-Markovnikov addition
of carboxylic acids to terminal alkynes gives valuable Z-enol esters. The
catalyst system is applicable to a broad substrate scope and displays a wide
functional group tolerance.
A. Lumbroso, N. R. Vautravers, B. Breit, Org. Lett., 2010,
12, 5498-5501.
PPh3AuCl/AgPF6-catalyzed hydroacyloxylation of alkynes
with carboxylic acids affords the Markonikov addition products, whereas PPh3AuCl/AgOTf
catalyst gives the more stable isomerized products via the Markonikov products.
B. C. Chary, S. Kim, J. Org. Chem., 2010,
75, 7928-7931.
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.
