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

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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 <b>2</b> were conveniently synthesized from reactions between anilide <b>1</b> and phenyliodine­(III) diacetate (PIDA) through hypervalent iodine mediated C­(sp<sup>2</sup>)–C­(sp<sup>2</sup>) 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.

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