Categories: C=O Bond Formation > Synthesis of ketones >
Synthesis of ketones by oxidation of alkenes
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Recent Literature
The synergistic effect of photocatalysis and proton-reduction catalysis enables
an unprecedented dehydrogenative oxygenation of β-alkyl styrenes and their
derivatives with water under external-oxidant-free conditions. This dual
catalytic system possesses the single anti-Markovnikov selectivity due to the
property of the visible-light-induced alkene radical cation intermediate.
G. Zhang, X. Hu, C.-W. Chiang, H. Yi, P. Pei, A. K. Singh, A. Lei, J. Am. Chem. Soc., 2016,
138, 12037-12040.
Utilizing the full potential of IBX, a mild, selective, and facile method
enables a direct conversion of olefins into the corresponding α-bromo ketones in
the presence of 1.1 equivalents each of o-iodoxybenzoic acid and
tetraethylammonium bromide.
S. S. Deshmukh, K. H. Chaudhari, K. G. Akamanchi, Synlett, 2011,
81-83.
In a Co-catalyzed reaction for the construction of 1,4-dicarbonyls, a cascade
organocobalt addition/trapping/Kornblum-DeLaMare rearrangement were involved.
The reaction offers easy availability of starting materials, wide substrate
scope, high functionality tolerance, and operational simplicity.
F. Zhang, P. Du, J. Chen, H. Wang, Q. Luo, X. Wan, Org. Lett., 2014,
16, 1932-1935.
Oxidative ring expansion of methylenecyclopropanes with CAN under oxygen
atmosphere was investigated. A facile conversion affording
2,2-diarylcyclobutanones occurred in good yields.
V. Nair, T. D. Suja, K. Mohanan, Synthesis, 2006, 2531-2534.
A practical and environmentally friendly method for the
oxidative rearrangement of five- and six-membered cyclic tertiary allylic
alcohols to α,β-unsaturated β-disubstituted ketones by IBX in DMSO
is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS)
are tolerated.
M. Shibuya, S. Ito, M. Takahashi, Y. Iwabuchi, Org. Lett., 2004, 6, 4303-4306.
Pd-catalyzed enantioselective diborations of prochiral allenes followed by
allylation reactions with primary imines provide vinyl boronates which may
be oxidized to give nonracemic Mannich products. Alternatively,
enantiomerically enriched homoallylic amine derivatives may be obtained by
protonation and Suzuki cross-coupling of the vinyl boronate.
J. D. Sieber, J. P. Morken, J. Am. Chem. Soc.,
2006, 128, 74-75.
An efficient method for the oxidation of an olefin to the less
substituted carbonyl compound is described. This one pot conversion
includes hydroboration with borane dimethyl sulfide (BDMS), followed by
oxidation of the resulting alkylboranes with tetrapropylammonium
perruthenate (TPAP) and NMO.
M. H. Yates, Tetrahedron Lett., 1997, 38, 2813-2816.
HTIB mediates an oxidative transposition of vinyl halides to provide α-halo
ketones as useful and polyvalent synthetic precursors. Insights into the
mechanism and an enantioselective transformation are reported too.
A. Jobin-Des Lauriers, C. Y. Legault, Org. Lett.,
2016,
18, 108-111.
An anthraquinone-catalyzed photooxidative keto-trifluoromethylation of
styrenes with the readily available Langlois reagent (CF3SO2Na)
under an oxygen atmosphere proceeds smoothly to give α-trifluoromethyl ketones
in good yield with good selectivity.
E. Yamaguchi, Y. Kamito, K. Matsuo, J. Ishihara, A. Itoh, Synthesis, 2018, 50,
3161-3168.
A copper/cobalt-catalyzed oxysulfonylation of alkenes with sulfonylazides and
tert-butyl hydroperoxide provides β-ketosulfones and β-sulfonyl peroxides
good yields under mild conditions. This methodology applies sulfonylazides as a
new sulfonyl radical source and features a wide substrate scope and good
functional group tolerance.
R. Chen, Y. Tang, X. He, K.-K. Wang, L. Ding, L. Liu, Org. Lett., 2023, 25,
5454-5458.
Related
An alternative pathway to the Wacker oxidation of internal olefins involving
epoxidation of trans-alkenes followed by a mild and highly regioselective
isomerization gives ketone isomers in good yield.
J. R. Lamb, M. Mulzer, A. M. LaPointe, G. W. Coates, J. Am. Chem. Soc., 2015,
137, 15049-15054.