Categories: I-O Bond Formation >
Synthesis of hypervalent iodine(III) compounds
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Recent Literature
The use of oxone in trifluoroacetic acid enables a general and convenient
synthesis of [bis(trifluoroacetoxy)iodo]arenes at room temperature. The
oxidation of perfluoroalkyl iodides gives [bis(trifluoroacetoxy)iodo]perfluoroalkanes,
that can be converted to stable [hydroxy(tosyloxy)iodo]perfluoroalkanes.
A. A. Zagulyaeva, M. S. Yusubov, V. V. Zhdankin, J. Org. Chem., 2010,
75, 2119-2122.
One-pot syntheses of neutral and electron-rich [hydroxy(tosyloxy)iodo]arenes (HTIBs)
from iodine and arenes avoid the need for expensive iodine(III) precursors. A
large set of HTIBs, including a polyfluorinated analogue, can be obtained from
the corresponding aryl iodides under mild conditions, without excess reagents,
in high yields.
E. A. Merritt, V. M. T. Carneiro, L. F. Silva Jr., B. Olofsson, J. Org. Chem., 2010,
75, 7416-7419.
Sodium perborate in acetic acid is an effective reagent for the oxidation of
aromatic aldehydes to carboxylic acids, iodoarenes to (diacetoxyiodo)arenes,
azines to N-oxides, and various sulphur heterocycles to S,S-dioxides.
Nitriles undergo smooth oxidative hydration to amides when aqueous methanol
is employed as solvent.
A. McKillop, D. Kemp, Tetrahedron, 1989,
45, 3299-3306.
A modified procedure for the direct synthesis of hypervalent [bis(trifluoroacetoxy)iodo]arenes
avoids the use of hazardous reagents with the workup being only an aqueous
extraction.
T. Keri Page, T. Wirth, Synthesis, 2006, 3080-3084.
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