用于乙烯基芳烃反马氏型碘代氧酰亚胺化反应的高价碘化合物。

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

作者信息

Krylov Igor B, Paveliev Stanislav A, Syroeshkin Mikhail A, Korlyukov Alexander A, Dorovatovskii Pavel V, Zubavichus Yan V, Nikishin Gennady I, Terent'ev Alexander O

机构信息

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation.

All-Russian Research Institute for Phytopathology, 143050 B. Vyazyomy, Moscow Region, Russian Federation.

出版信息

Beilstein J Org Chem. 2018 Aug 16;14:2146-2155. doi: 10.3762/bjoc.14.188. eCollection 2018.

The iodo-oxyimidation of styrenes with the -hydroxyimide/I/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc) proved to be the most effective; yields of iodo-oxyimides are 34-91%. A plausible reaction pathway includes the addition of an imide--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.