Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of carboxylic acids, esters and amides
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Recent Literature
The presence of LICl enabled an efficient process for the carboxylation of
functionalized organozinc reagents with CO2 in DMF as solvent.
K. Kobayashi, Y. Kondo, Org. Lett., 2009,
11, 2035-2037.
A variety of functionalized organozinc reagents undergo smooth addition
reactions at ambient temperature to carbonyl compounds and carbon dioxide in the
presence of stoichiometric amounts of MgCl2. Several reactions were
performed on a large scale.
S. Bernhardt, A. Metzger, P. Knochel, Synthesis, 2010, 3802-3810.
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 nickel-catalyzed reductive carboxylation of styrenes using CO2
proceeds under mild conditions using diethylzinc as the reductant. The catalyst
system is very robust and will fixate CO2 in good yield even if
exposed to only an equimolar amount introduced into the headspace above the
reaction.
C. M. Williams, J. B. Johnson, T. Rovis, J. Am. Chem. Soc., 2008,
130, 14936-14937.
Pd-catalyzed carbonylation of α-diazocarbonyl compounds or N-tosylhydrazone
salts under atmospheric pressure of CO enables an efficient and mild approach
toward ketene intermediates. These ketenes can react in situ with various
nucleophiles to yield carboxylic acid derivates or in Staudinger cycloadditions
to give β-lactam derivatives in good yields with excellent trans
diastereoselectivity.
Z. Zhang, Y. Liu, L. Ling, Y. Li, Y. Dong, M. Gong, X. Zhao, Y. Zhang, J. Wang, J. Am. Chem. Soc., 2011,
133, 4330-4341.
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.
PSiP-pincer type palladium-catalyzed hydrocarboxylation enables an efficient
one-to-one coupling reaction of atmospheric pressure carbon dioxide with
1,3-dienes. The reaction represents a highly useful method for the synthesis of
β,γ-unsaturated carboxylic acid derivatives from CO2 and various
1,3-dienes including easily available chemical feedstock such as 1,3-butadiene
and isoprene.
J. Takaya, K. Sasano, N. Iwasawa, Org. Lett., 2011,
13, 1698-1701.
A tridentate PSiP pincer-type palladium complex-catalyzed hydrocarboxylation of
allenes under carbon dioxide gives synthetically useful β,γ-unsaturated
carboxylic acids. This novel CO2-fixation proceeds via
hydropalladation of allenes, followed by regioselective nucleophilic addition to
CO2 in the presence of an appropriate reducing agent. Esters,
carbamates, ketones, and alkenes are tolerated.
J. Takaya, N. Iwasawa, J. Am. Chem. Soc., 2008,
130, 15254-15255.
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.
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.
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.
