Sodium Chlorite
Recent Literature
Sodium chlorite is an efficient stoichiometric oxidant in Sharpless
asymmetric dihydroxylation. The conversion of styrene was achieved twice as fast
as in the established Sharpless K3[Fe(CN)6]
dihydroxylation. Eight olefins were dihydroxylated to corresponding vicinal
diols with yields and ees as good as those reported in the literature for other
similar processes.
M. H. Junttila, O. E. O. Hormi, J. Org. Chem., 2004, 69,
4816-4820.
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.
A mild one-pot ozonolysis-oxidation process enables the synthesis of carboxylic
acids from alkenes. Conducting the ozonolysis in an aqueous organic solvent
eliminates secondary ozonide formation and the intermediates generated are
readily converted into a carboxylic acid by adding sodium chlorite. The desired
acids are isolated in high purity and high yield by simple extraction after a
reductive quench.
B. M. Cochran,
Synlett, 2016, 27, 245-248.
Catalytic amounts of TEMPO and NaOCl enable a chemoselective oxidation of
1,2-diols to in the presence of NaClO2 as terminal oxidant. The use
of a two-phase condition suppresses the concomitant oxidative cleavage. The
observed selectivity seems to be derived from the precise solubility control of
diols and hydroxy acids as well as the charge transfer complex TEMPO-ClO2,
which dissolves into the organic layer.
K. Furukawa, M. Shibuya, Y. Yamamoto, Org. Lett.,
2015,
17, 2282-2285.
A direct enantioselective α-hydroxymethylation of aldehydes employing an
α,α-diarylprolinol trimethylsilyl ether organocatalyst enables efficient access
to β-hydroxycarboxylic acids and δ-hydroxy-α,β-unsaturated esters via an
intermediate lactol in good yields, excellent enantioselectivity, and
compatibility with a broad range of functional groups in the aldehyde.
R. K. Boeckman, K. F. Biegasiewicz, D. J. Tusch, J. R. Miller, J. Org. Chem.,
2015,
80, 4030-4045.
A simple NaClO2-mediated oxidative chlorosulfonation of S-alkyl
isothiourea salts enables a convenient, safe, and environmentally benign
synthesis of diverse sulfonyl chlorides in high yields. The procedure is also
applicable to other substrates such as thiols, disulfides, thioacetates, and
xanthates.
Z. Yang, Y. Zheng, J. Xu, Synlett, 2013, 24,
2165-2169.
The use of cheap and innocuous reagents, such as NaClO2, NaOCl,
and catalytic amounts of TEMPO enables an environmentally friendly C(sp3)-H
oxidation of piperazines and morpholines to 2,3-diketopiperazines and
3-morpholinones, respectively. In addition, by using a stoichiometric amount of
TEMPO, 2-alkoxyamino-3-morpholinones can be prepared from morpholine derivatives.
D. Chamorro-Arenas, U. Osorio-Nieto, L. Quintero, L. Hernández-García, F.
Sartillo-Piscil, J. Org. Chem., 2018, 83,
15333-15346.
