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Synthesis of substituted carboxylic acids, esters and amides

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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.