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Synthesis of substituted carboxylic acids, esters and amides

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Arndt-Eistert Synthesis


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.