Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of substituted carboxylic acids, esters and amides
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Name Reactions
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.
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.
