Categories: C-C Bond Formation > Oxygen-containing molecules >
Synthesis of substituted carboxylic acids, esters and amides
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Recent Literature

A general, inexpensive, copper-catalyzed coupling of terminal alkynes
with diazo compounds has been developed. This reaction, which proceeds
efficiently under nonbasic conditions at room temperature, tolerates various
functional groups.
A. Suarez, G. C. Fu, Angew. Chem., 2004,
116, 3664-3666.
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.

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.

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. Jørgensen, S. Lee, X. Liu, J. P. Wolkowski, J. F. Hartwig, J. Am.
Chem. Soc., 2002,
124, 12557-12565.


