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.