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Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes.

ABSTRACT: The iodo-oxyimidation of styrenes with the N-hydroxyimide/I2/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34-91%. A plausible reaction pathway includes the addition of an imide-N-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine. It was shown that the iodine atom in the prepared iodo-oxyimides can be substituted by various nucleophiles.

SUBMITTER: Krylov IB 

PROVIDER: S-EPMC6122379 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes.

Krylov Igor B IB   Paveliev Stanislav A SA   Syroeshkin Mikhail A MA   Korlyukov Alexander A AA   Dorovatovskii Pavel V PV   Zubavichus Yan V YV   Nikishin Gennady I GI   Terent'ev Alexander O AO  

Beilstein journal of organic chemistry 20180816

The iodo-oxyimidation of styrenes with the <i>N</i>-hydroxyimide/I<sub>2</sub>/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)<sub>2</sub> proved to be the most effective; yields of iodo-oxyimides are 34-91%. A plausible reaction pathway includes the addition of an imide-<i>N</i>-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine. It was shown that the iodine atom in the prepa  ...[more]

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