Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of substituted carboxylic acids, esters and amides
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Recent Literature
Indium(III) halide catalyzed the coupling of alkyl chlorides with silyl enolates
derived from esters, ketones, and aldehydes to give various α-alkylated carbonyl
compounds. A one-pot, three-component reactions of aldehyde enolates, alkyl
chlorides, and allylsilanes or alkynylsilanes is described.
Y. Nishimoto, M. Yasuda, A. Baba, Org. Lett., 2007,
9, 4931-4934.
Carboindation of various alkenes such as ethylene, 1-alkenes, and cyclic alkenes
with indium tribromide enables a regioselective reaction with ketene silyl
acetals. The alkylindium product from the carboindation of cyclohexene revealed
an anti addition mechanism.
Y. Nishimoto, H. Ueda, Y. Inamoto, M. Yasuda, A. Baba, Org. Lett., 2010,
12, 3390-3393.
A general, inexpensive, copper-catalyzed coupling of terminal alkynes with
diazo compounds provides ready access to 3-alkynoates. This reaction proceeds efficiently
under nonbasic conditions at room temperature and tolerates various functional
groups.
A. Suárez, G. C. Fu, Angew. Chem. Int. Ed., 2004, 43,
3580-3582.
A radical alkenylation reaction of α-halo carbonyl compounds with
styrylindium dichloride as well as unactivated alkenylindiums proceeded in
the presence of triethylborane. The geometry of the carbon-carbon double
bonds was retained. Efficient one-pot strategies were developed.
K. Takami, H. Yorimitsu, K. Oshima, Org. Lett.,
2004,
6, 4555-4558.
Acrylamide and aromatic aldehydes were found to undergo the Baylis-Hillman
reaction at ambient temperature and pressure in an aqueous medium in the
presence of a stoichiometric amount of DABCO, to give the corresponding
3-hydroxy-2-methylenepropionamides in excellent yield. A faster, but
reversible side reaction gave N-acylhemiaminals, which later
disappeared, as the desired Baylis-Hillman adducts were formed as major
products over an extended period of time.
C. Yu, L. Hu, J. Org. Chem., 2002, 67, 219-223.
A palladium-catalyzed coupling of aryl halides and ester enolates produced
α-aryl esters in high yields at room temperature. The reaction was highly
tolerant of functionalities and substitution patterns on the aryl halide.
Improved protocols for the selective monoarylation of tert-butyl
acetate and the efficient arylation of α,α-disubstituted esters were
developed with LiNCy2 as base and P(t-Bu)3 as ligand.
M. Jřrgensen, S. Lee, X. Liu, J. P. Wolkowski, J. F. Hartwig, J. Am.
Chem. Soc., 2002,
124, 12557-12565.
