Categories: I-O Bond Formation >
Synthesis of hypervalent iodine(III) compounds
| Related: |  |
Recent Literature
Sodium hypochlorite pentahydrate (NaClO·5H2O) enables an
inexpensive, safe, and rapid oxidation of iodoarenes to provide synthetically
useful (diacetoxyiodo)arenes as precursors of various organo-λ3-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.
A. Watanabe, K. Miyamoto, T. Okada, T. Asawa, M. Uchiyama, J. Org. Chem., 2018, 83,
14262-14268.
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.
Various [(diacetoxy)iodo]arenes were efficiently prepared by the treatment of
iodoarenes with m-chloroperoxybenzoic acid in acetic acid. The great
advantage of the present method is the easy preparation and isolation of [(diacetoxy)-iodo]arenes
bearing electron-withdrawing groups.
M. Iinuma, K. Moriyama, H. Togo, Synlett, 2012, 23,
2663-2666.
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.
| Related:
|
