Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of carboxylic acids, esters and amides
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Recent Literature
An efficient cross-coupling reaction of chloroformates with organocopper
reagents, derived from Grignard reagents, cuprous bromide and lithium bromide,
provides esters in good yields.
D. Bottalico, V. Fiandanese, G. Marchese, A. Punzi, Synlett, 2007,
974-976.
The reaction of Grignard reagents with alkyl imidazolecarboxylates, which
were prepared from alcohols with carbonyl diimidazole, gave the
corresponding esters in good to excellent yields.
T. Werner, A. G. M. Barrett, J. Org. Chem., 2006,
71, 4302-4304.
A mild, Co2(CO)8-catalyzed carbonylative opening of
terminal epoxides under 1 atm of carbon monoxide at room temperature in methanol
provides β-hydroxy esters in good yields. This transformation tolerates
various functional groups.
S. E. Denmark, M. Ahmad, J. Org. Chem., 2007,
72, 9630-9634.
The reaction of chiral 1-aminoalkylepoxides with CO2, generated from
acidic treatment of an aqueous solution of NaHCO3 at room temperature,
efficiently afforded enantiopure cyclic carbonates with total selectivity.
Carbonates were readily transformed into the corresponding diols by reaction
with LiAlH4 or by basic hydrolysis.
J. M. Concellón, V. del Solar, S. Carcía-Granda, M. R. Díaz, J. Org. Chem.,
2007,
72, 7567-7568.
Alkylboranes, generated by hydroboration of terminal olefins with 9-BBN-H,
underwent smooth coupling with carbamoyl chlorides in the presence of palladium
catalyst and Cs2CO3 to give C1-elongated amides.
Y. Yasui, S. Tsuchida, H. Miyabe, Y. Takemoto, J. Org. Chem., 2007,
72, 5898-5900.
The presence of catalytic amounts of halide salts enhanced dramatically the
reaction efficiency in the Ru-catalyzed hydroesterification of alkenes and
alkynes using a chelating 2-pyridylmethyl formate.
E. J. Park, J. M. Lee, H. Han, S. Chang, Org. Lett.,
2006,
8, 4355-4358.
Treatment of 2,2-dimethylpropan-1,3-diol esters of aryl- and alkenylboronic
acids with a catalytic amount of [Rh(OH)(cod)]2 in the presence
of 1,3-bis(diphenylphosphino)propane and CsF in dioxane at 60°C under carbon
dioxide atmosphere gave carboxylic acids in good yields.
K. Ukai, M. Aoki, J. Takaya, N. Iwasawa, J. Am. Chem. Soc.,
2006,
128, 8706-8707.
The palladium-catalyzed cross-coupling of allylic and benzylic halides with
N,N-dimethylcarbamoyl(trimethyl)silane affords tertiary amides in good to
excellent yields.
R. F. Cunico, R. K. Pandey, J. Org. Chem., 2005,
70, 9048-9050.
Thiourea-based ligands were evaluated for the palladium-catalyzed
bis(methoxycarbonylation) of terminal olefins. The usefulness of these
ligands for this reaction is demonstrated by their stability to oxidizing
agents, and their superiority in preventing palladium precipitation and
double-bond isomerization.
M. Dai, C. Wang, G. Dong, J. Xiang, T. Luo, B. Liang, J. Chen, Z. Yang,
Eur. J. Org. Chem., 2003, 4346-4348.
α-Halonitriles react with alkyllithium, organomagnesium, and lithium
dimethylcuprate reagents generating reactive, metalated nitriles. The rapid
halogen-metal exchange with alkyllithium and Grignard reagents allows
Barbier-type reactions with various electrophiles.
F. F. Fleming, Z. Zhang, W. Liu, P. Knochel, J. Org. Chem., 2005,
70, 2200-2005.
The Brønsted acid catalyzed formal insertion of an isocyanide into a C-O bond
of various acyclic and cyclic acetals can be applied to form α-alkoxy imidates.
Functional groups, such as nitro, cyano, halogen, ester, and alkoxy groups, are
tolerant to the reaction conditions employed. The course of the reaction is
highly dependent on the structure of the isocyanide.
M. Tobisu, A. Kitajima, S. Yoshioka, I. Hyodo, M. Oshita, N. Chatani, J. Am. Chem. Soc.,
2007, 129, 11431-11437.
