Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds
Synthesis of Carbonyl Compounds by Alkylation or Condensation
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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.
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.
Photoirradiation of a mixture of acetone and water containing olefins affords
the corresponding methyl ketones efficiently via a water-assisted C-C coupling
between the acetonyl radical and olefins.
Y. Shiraishi, D. Tsukamoto, T. Hirai, Org. Lett.,
2008,
10, 3117-3120.
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. Int. Ed.,
2005, 44, 6924-6927.
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 synergistic combination of copper and chiral amine catalysis enables an
enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts.
These mild catalysis provides enolizable α-formyl vinylic stereocenters without
racemization or olefin transposition. These high-value coupling adducts are
readily converted into various useful olefin synthons.
E. Skucas, D. W. C. MacMillan, J. Am. Chem. Soc., 2012,
134, 9090-9093.
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.
