Sodium periodate
See also: potassium periodate
Recent Literature
A ruthenium catalyst bearing a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based
abnormal N-heterocyclic carbene ligand enables a selective oxidation of C═C
bonds in a broad range of substrate to aldehydes and C≡C bonds to α-diketones in
an EtOAc/CH3CN/H2O solvent mixture at room temperature.
P. Daw, R. Petakamsetty, A. Sarbajna, S. Laha, R. Ramapanicker, J. K. Bera,
J. Am. Chem. Soc., 2014,
136, 13987-13990.
Osmium tetroxide has been microencapsulated in a polyurea matrix. These
microcapsules have been effectively used as recyclable catalysts in the
dihydroxylation and the oxidative cleavage of olefins.
S. V. Ley, C. Ramarao, A.-L. Lee, N. Ostergaard, S. C. Smith, I. M.
Shirley, Org. Lett., 2003, 5, 185-187.
Specific oxidation protocols have been developed for the cleavage of styrenes,
aliphatic olefins, and terminal aliphatic olefins to carbonyl compounds with
ruthenium trichloride as catalyst. Olefins that are not fully substituted are
converted to aldehydes rather than carboxylic acids.
D. Yang, C. Zhang, J. Org. Chem., 2001, 66,
4814-4818.
A catalytic amount of a composite material, RuO2/BaTi4O9,
in combination with NaIO4 in EtOAc-H2O has been shown to
efficiently cleave alkenes, affording ketones, aldehydes and/or carboxylic acids
in high yields.
H. Okumoto, K. Ohtsuko, S. Banjoya, Synlett, 2007,
3201-3205.
A high-yielding, asymmetric synthesis of novel 4-formyl-1-(2- and
3-haloalkyl)azetidin-2-ones was developed as valuable starting materials for the
synthesis of different enantiomerically enriched bicyclic azetidin-2-ones, such
as piperazine, morpholine, and 1,4-diazepane annulated β-lactam derivatives.
W. Van Brabandt, M. Vanwalleghem, M. D'hooghe, N. De Kimpe, J. Org. Chem., 2006,
71, 7083-7086.
An improved protocol for the RuO4-catalyzed syn-dihydroxylation
uses only 0.5 mol% catalyst under acidic conditions. Various olefins can be
hydroxylated in good to excellent yields with only minor formation of side
products.
B. Plietker, M. Niggemann, Org. Lett., 2003, 3353-3356.
LiBr is an efficient catalyst for the dihydroxylation of alkenes to afford
either syn or anti diols with excellent diastereoselectivity
depending upon the use of NaIO4 or PhI(OAc)2 as the
oxidants.
L. Emmanuvel, T. M. A. Shaikh, A. Sudalai, Org. Lett.,
2005,
7, 5071-5074.
Grubbs' 2nd generation metathesis catalyst can be used in tandem olefin
metathesis/oxidation protocols. These ruthenium-catalyzed processes provide
access to cis-diols or α-hydroxy ketones from simple olefinic starting
materials.
A. A. Scholte, M. H. An, M. L. Snapper, Org. Lett.,
2006,
8, 4759-4762.
A new one-pot method is described for the removal of O- and N-allyl
protecting groups under oxidative conditions at near neutral pH. The
allyl group undergoes hydroxylation and subsequent periodate scission of
the vicinal diol. Repetition of this reaction sequence on the enole
tautomer of the aldehyde intermediate releases the deprotected
functional group.
P. I. Kitov, D. R. Bundle, Org. Lett., 2004, 3,
2835-2838.
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 highly
enantioselective and catalytic vinylation of aldehydes leads to allylic alcohols
that are then transformed to the allylic amines via Overman's [3,3]-sigmatropic
rearrangement of imidates. Oxidative cleavage of the allylic amines furnishes amino acids in good yields and excellent ee's. The scope and utility of this
method are demonstrated by the synthesis of challenging allylic amines and their
subsequent transformation to valuable nonproteinogenic amino acids, including
both D and L configured (1-adamantyl)glycine.
Y. K. Chen. A. E. Lurain, P. J. Walsh, J. Am. Chem. Soc., 2002,
124, 12225-12231.
The combination of sodium periodate, potassium iodide, and sodium azide is an
efficient, simple, and inexpensive reagent system for azidoiodination of
alkenes. The regiospecific 1,2-azidoiodination proceeds in an anti-Markovnikov
fashion to produce β-iodoazides in excellent yields.
P. V. Chouthaiwale, P. U. Karabal, G. Suryavanshi, A. Sudalai, Synthesis, 2010,
3879-3882.
Deactivated arenes were mono- or diiodinated with strong electrophilic I+
reagents, which were prepared from NaIO4 and either I2
or KI in concentrated sulfuric acid, using either a ‘direct’ or an ‘inverse’
method of aromatic iodination to give mono- or diiodinated pure products in
good yields.
L. Kraszkiewicz, M. Sosnowski, L. Skulski,
Synthesis, 2006, 1195-1199.
A novel, high-yielding method for sulfation of alcohols proceeds via
sulfite- and sulfate diester intermediates. Sulfite diesters serve as
versatile sulfate monoester precursors, that allow interesting
transformations.
M. Huibers, I. Manuzi, F. P. J. T. Rutjes, F. L. van Delft, J. Org. Chem., 2006,
71, 7473-7476.
The reaction of alkenes with sodium arene sulfinates in the presence of
potassium iodide and sodium periodate and a catalytic amount of acetic acid
provides vinyl sulfones at room temperature. The products are formed in high
yields within hours.
B. Das, M. Lingaiah, K. Damodar, N. Bhunia, Synthesis, 2011,
2941-2644.
Arylboronic acids and aryl trifluoroborates are synthesized in a one-pot
sequence by Ir-catalyzed borylation of arenes. To prepare the arylboronic acids,
the Ir-catalyzed borylation is followed by oxidative cleavage of the pinacol
boronates with NaIO4. To prepare the aryltrifluoroborate, the
Ir-catalyzed borylation is followed by displacement of pinacol by KHF2.
J. M. Murphy, C. C. Tzschucke, J. F. Hartwig, Org. Lett., 2007,
9, 757-760.
RuCl3·3H2O catalyzes an oxidative dearomatization of
N-Boc indoles into indolin-3-ones in acetonitrile using sodium periodate as
oxidant.
X. Chen, X.-Y. Zhou, X.-J. Feng, M. Bao, Synthesis, 2021, 53,
1121-1126.