Categories: C=O Bond Formation > Synthesis of ketones >
Synthesis of ketones by oxidation of benzylic substrates
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The use of NaClO/TEMPO/Co(OAc)2 enabled a benzylic oxidation of alkyl
arenes to yield various aromatic aldehydes and ketones in very good yields. The
reaction reactivity, selectivity, and scope of the reaction were investigated.
C. Jin, L. Zhang, W. Su, Synlett, 2011,
1435-1438.
The cationic complex [(pymox-Me2)RuCl2]+BF4-
is a highly effective catalyst for the C-H bond oxidation of aryl alkanes in
water using tert-butyl
hydroperoxide as oxidant to yield various aryl ketones at room temperature in
water as solvent. A solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo
intermediate species is suggested.
C. S. Yi, K.-H. Kwon, D. W. Lee, Org. Lett., 2009,
11, 1567-1569.
o-Iodoxybenzoic acid (IBX) was found to be highly effective in oxidations
adjacent to carbonyl and benzylic functionalities to form either α,β-unsaturated carbonyl compounds
or conjugated aromatic carbonyl systems. Fine-tuning of the
reaction conditions allowed remarkably selective transformations within
multifunctional substrates.
K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc., 2002, 124, 2245-2258.
Permanganate supported on active manganese dioxide can
be used effectively for the oxidation of
arenes, alcohols and sulfides under heterogeneous
or solvent-free conditions.
A. Shaabania, P. Mirzaeia, S. Naderia, D. G. Leeb, Tetrahedron, 2004, 60, 11415-11420.
The bismuth and picolinic acid-catalyzed oxidation of alkyl arenes with tert-butyl hydroperoxide in pyridine and acetic acid gave benzylic
ketones in good yields. Alternatively, oxidation of methyl
arenes gave the corresponding substituted benzoic acids. A radical mechanism is
discussed.
Y. Bonvin, E. Callens, I. Larrosa, D. A. Henderson, J. Oldham, A. J. Burton,
A. G. M. Barrett, Org. Lett.,
2005, 7, 4549-4552.
An efficient oxidant-free oxidation for a wide range of alcohols was
achieved by a recyclable ruthenium catalyst, which was prepared from readily
available reagents through nanoparticle generation and gelation.
W.-H. Kim, I. S. Park, J. Park, Org. Lett.,
2006, 8, 2543-2545.
