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Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds

Synthesis of Carbonyl Compounds by Alkylation or Condensation

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Acetoacetic Ester Synthesis


Mannich Reaction


Recent Literature


A highly efficient α alkylation of ketones with primary alcohols by the use of a recyclable palladium catalyst has been demonstrated.
M. S. Kwon, N. Kim, S. H. Seo, I. S. Park, R. K. Cheedrala, J. Park, Angew. Chem., 2005, 117, 7073-7075.


The Cu(acac)2-catalyzed cross-coupling of alkylzinc halides with α-chloroketones introduces primary and secondary alkyl groups adjacent to a ketone carbonyl under mild reaction conditions and in good yield. The reaction proceeds stereospecifically with inversion of stereochemistry.
C. F. Malosh, J. M. Ready, J. Am. Chem. Soc., 2004, 126, 10240-20241.


A simple method for the chemo- and regioselective, direct catalytic allylic alkylation of aldehydes and cyclic ketones has been developed. The combination of palladium and enamine catalysis furnished α-allylic alkylated aldehydes and cyclic ketones in high yields.
I. Ibrahem, A. Córdova, Angew. Chem. Int. Ed., 2006, 45, 1952-1956.


A catalytic enantioconvergent synthesis of quaternary stereocenters from racemates with quaternary stereocenters has been developed. A chiral Pd catalyst is involved in both the stereoablative (C-C bond-breaking) and stereoselective (C-C bond-forming) steps.
J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem., 2005, 117, 7084-7087.


An efficient and highly enantioselective conjugate addition of alkylzinc reagents to various cyclic nitroalkenes is promoted in the presence of 0.5-5 mol % (CuOTf)2·C6H6 and 1-10 mol % of chiral amino acid-based phosphine ligands at 0°C in toluene. Depending on the reaction conditions used, either the nitro or the corresponding α-substituted ketone product can be accessed.
C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc., 2002, 124, 8192-8193.


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.


Multifunctional palladium catalysis allows a one-pot stereocontrolled synthesis of tetrasubstituted methyl ketones and enynes. The homogeneous palladium dihalide catalyst is used for the bromo-/chloroallylation of alkynes and in situ for subsequent Wacker-Tsuji oxidation or Sonogashira cross-coupling.
A. N. Thadani, V. H. Rawal, Org. Lett., 2002, 4, 4321-4323.