Categories: C-O Bond Formation > Synthesis of carboxylic acids >
Synthesis of carboxylic acids by oxidative cleavages and rearrangements
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Recent Literature
A facile synthesis of aryl carboxylic acids from aryl ketones by aerobic
photooxidation using the inexpensive and easily handled CBr4 as
catalyst is applicable to inert compounds under usual photo-irradiation
conditions, and appears very attractive for the expansion of the Norrish Type I
reaction.
S.-i. Hirashima, T. Nobuta, N. Tada, A. Itoh, Synlett, 2009,
2017-2019.
A mixture of Oxone and trifluoroacetic acid enables a simple and mild metal-free
oxidation of various ketones or arylalkynes to the corresponding carboxylic
acids in excellent yields.
K. A. A. Kumar, V. Venkateswarlu, R. A. Vishwakarma, S. D. Sawant,
Synthesis, 2015, 47, 3161-3168.
A metal-free and one-pot two-step synthesis of aryl carboxylic acids from aryl
alkyl ketones has been performed with iodine as the catalyst, DMSO and TBHP as
the oxidants. Various aryl alkyl ketones could be converted into their
corresponding aryl carboxylic acids in very good yields.
L. Xu, S. Wang, B. Chen, M. Li, X. Hu, B. Hu, L. Jin, N. Sun, Z. Shen,
Synlett, 2018, 29, 1505-1509.
Diphenyl diselenide catalyzes an oxidative degradation of benzoins to benzoic
acids under mild conditions.
H. Cao, T. Chen, C. Yang, J. Ye, X. Zhang, Synlett, 2019,
30,
1683-1687.
Oxone oxidatively degrades 1,3-dicarbonyl compounds and α-hydroxy ketones to
carboxylic acids. This method compliments existing methodologies and is in
general a milder alternative to the haloform reaction.
S. W. Ashford, K. C. Grega, J. Org. Chem., 2001,
66, 1523-1524.
An I2-promoted direct conversion of arylacetic acids into aryl
carboxylic acids under metal-free conditions involves decarboxylation followed
by an oxidation reaction enabled just by using DMSO as the solvent as well as an
oxidant. Notably, aryl carboxylic acids are isolated by simple filtration
technique and obtained in good to excellent yields, which makes this protocol
applicable for large-scale synthesis.
H. P. Kalmode, K. S. Vadagaonkar, S. L. Shinde, A. C. Chaskar, J. Org. Chem.,
2017, 82, 3781-3786.
A catalytic, asymmetric conjugate addition of carbamates to enoyl systems provides a highly enantioselective two-step
access to N-protected β-amino acids.
C. Palomo, M. Oiarbide, R. Halder, M. Kelso, E. Gómez-Bengoa, J. García, J. Am. Chem. Soc.,
2004,
126, 9188-9189.
A catalytic oxidative cleavage of 1,3-diketones enables the synthesis of the
corresponding carboxylic acids by aerobic photooxidation with iodine under
irradiation with a high-pressure mercury lamp.
N. Tada, M. Shomura, L. Cui, T. Nobuta, T. Miura, A. Itoh, Synlett, 2011,
2896-2900.
A mild, fast protocol for the conversion of β-ketoesters and β-diketones to
carboxylic acids with use of CAN in CH3CN is described. The
method is compatible with a number of functional groups, and can generate
carboxylic acids under neutral conditions. The mechanism is discussed.
Y. Zhang, J. Jiao, R. A. Flowers, II, J. Org. Chem., 2006,
71, 4516-4520.
D. Yang, C. Zhang, J. Org. Chem., 2000, 66, 4814-4818.
A smooth, organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to
one-carbon-unit-shorter carboxylic acids is catalyzed by 1-Me-AZADO in the
presence of a catalytica amount of NaOCl and NaClO2 under mild
conditions. A broad range of substrates including carbohydrates and N-protected
amino diols were converted without epimerization.
M. Shibuya, R. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi, Org. Lett., 2012,
14, 5006-5009.
An aerobic photooxidative cleavage of vicinal diols yields carboxylic acids
using 2-chloroanthraquinone in the presence of photoirradiation with a
high-pressure mercury lamp. This is a metal-free reaction in which molecular
oxygen is used as the terminal oxidant.
Y. Matsusaki, T. Yamaguchi, N. Tada, T. Miura, A. Itoh, Synlett, 2012, 23,
2059-2062.