American Chemical Society
Browse

Metal-Free Synthesis of 2‑Oxindoles via PhI(OAc)2‑Mediated Oxidative C–C Bond Formation

Download (12.98 kB)
dataset
posted on 2014-02-07, 00:00 authored by Jinglei Lv, Daisy Zhang-Negrerie, Jun Deng, Yunfei Du, Kang Zhao
The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions between anilide 1 and phenyliodine­(III) diacetate (PIDA) through hypervalent iodine mediated C­(sp2)–C­(sp2) bond formation followed by a subsequent deacylation reaction. This metal-free method, shown to provide direct access to an important oxindole intermediate, could be applied to the total synthesis of naturally occurring horsfiline.

History

Usage metrics

    The Journal of Organic Chemistry

    Categories

    Keywords

    PhIPIDAseriesmonofunctionalizedphenyliodineaccessOxindolemethodSynthesioxindoleOxidativeformationBondhypervalent iodinehorsfilineFormationTheanilide 1diacetatesynthesisdeacylation reactionbond

    Licence

    CC BY-NC 4.0

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC