Categories: C=O Bond Formation >
Synthesis of ketones
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Reactions
Oxidation of alcohols
Oxidation of benzylic positions
Oxidation of alkenes
Cleavage of alkenes
Reaction of alkynes
Isomerisations
Hydrolysis or deprotection
Hydrolysis of enol ethers
Recent Literature
A hypervalent iodine reagent, (diacetoxyiodo)benzene, and catalytic amount of
sodium azide in acetonitrile enable an oxidative decarboxylation of 2-aryl
carboxylic acids into the corresponding aldehydes, ketones, and nitriles in good
yields at room temperature. The advantages of this protocol are short reaction
times and mild reaction conditions.
V. N. Telvekar, K. A. Sasane, Synlett, 2010,
2778-2779.
Reactivity at the homobenzylic position can be accomplished using dual organic
photoredox/cobalt catalysis. Through a two-part catalytic system, alkyl arenes
undergo dehydrogenation followed by an anti-Markovnikov Wacker-type oxidation to
provide benzyl ketone products. This formal homobenzylic oxidation is
accomplished with high atom economy without the use of directing groups.
J. B. McManus, J. D. Griffin, A. R. White, D. A. Nicewicz, J. Am. Chem. Soc.,
2020, 142, 10325-10330.
A copper-catalyzed oxidative cleavage reaction of terminal and internal
alkynes using NFSI and TBHP provides aryl ketone products in good yields. NFSI
not only functioned as N-centered radical precursor but also engaged in
the aryl group migration. Mechanistic studies also suggested the important role
of water.
L. Tang, F. Yang, H. Cheng, C. Tan, C. Jin, H. Chen, Y. Huang, S. Zhang, S.
Zhang, W. Song, J. Tan,
Org. Lett., 2020, 22, 8618-8623.
A radical-based C-C bond scission of 1,1-disubstituted epoxides followed by
demethylenation provides ketones. The reaction is accomplished by Selecfluor and its radical dication working in tandem.
E. Holt, N. G. Garrison, R. Rowshanpour, J. J. Kim, N. Henriquez, W. Lam, N.
Kiame, J. Williams, S. Zhao, T. Dudding, T. Lectka, J. Org. Chem., 2023, 88,
7597-7600.
The use of visible-light-induced silver catalysis enables a controlled
singlet-oxygen-mediated selective C-S bond cleavage reaction of benzyl thiols to
afford carbonyl compounds.
B. Hong, K. C. C. Aganda, A. Lee,
Org. Lett., 2020, 22, 4395–4399.
A commercial cyclopentadienylrutenium dicarbonyl dimer efficiently catalyzes the
formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy
azides via C-C bond cleavage under visible light.
J. Min Lee, D. Y. Bae, J. Y. Park, H. Y. Jo, E. Lee, Y. H. Rhee, J. Park,
Org. Lett., 2020, 22, 4608-4613.
Iron(III) acetylacetonate catalyzes an oxidative ring opening of cyclic
ethers and acetals under visible light irradiation with unparalleled efficiency.
This photocatalytic radical chemistry approach enables the conversion of
relatively inert cyclic ethers into useful synthetic intermediates and
illustrates that simple Fe(III) complexes can initiate redox processes from
4LMCT excited states.
R. Lindroth, A. Ondrejková, C.-J. Wallentin, Org. Lett.,
2022, 24, 1662-1667.
An oxidative alkyne translocation of readily accessible homopropargylic
alcohols provides unsymmetrical but-2-yne-1,4-diones in good yields via an
unprecedented one-pot sequential electro-oxidative
annulation-fragmentation-chemical selenoxide elimination process. Excellent
functional group compatibility was observed.
A. Halder, D. Maiti, J. Dutta, S. D. Sarkar, Org. Lett., 2023, 25,
7578-7583.