Beilstein J. Org. Chem.2022,18, 1672–1695, doi:10.3762/bjoc.18.179
in the case of chelating substrates [80]. In order to avoid the usage of transition metal salts, metal-free oxidative systems for the generation of imide-N-oxylradicals were proposed. In the majority of such systems, an N-hydroxyimide undergoes single-electron oxidation photochemically by a
homogeneous process, which once initiated on the TiO2 surface, can produce multiple molecules of product without additional light absorption.
Another approach to the generation of imide-N-oxylradicals under mild conditions without transition metal salts as co-catalysts employs electric current as the oxidant
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Graphical Abstract
Scheme 1:
Organocatalysis classification used in the present perspective.
Beilstein J. Org. Chem.2018,14, 2146–2155, doi:10.3762/bjoc.14.188
. It was shown that the iodine atom in the prepared iodo-oxyimides can be substituted by various nucleophiles.
Keywords: free radicals; hypervalent iodine; imide-N-oxylradicals; iodination; N-hydroxyimides; oxidative functionalization; Introduction
The presented work opens a new chapter in the
chemistry of N-hydroxyimides in combination with hypervalent iodine compounds with formation of imide-N-oxylradicals. These radicals were used as reagents for the addition to a terminal position of the double bond of styrenes with subsequent iodination of the resulting benzylic radical.
It is important to
imide-N-oxylradicals are used as effective mediators for CH-functionalization with formation of C–C, C–O, C–S, and C–N bonds [11][16][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42].
Phthalimide-N-oxyl (PINO) is one of the most known imide-N-oxyl
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Graphical Abstract
Scheme 1:
Difunctionalization of double C=C bond with the formation of C–O and C–I bonds.