4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 3, Pages 1111-1119

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo4025539

Keywords

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Funding

  1. National Natural Science Foundation of China [21072148]
  2. Foundation (B) for Peiyang Scholar-Young Core Faculty of Tianjin University [2013XR-0144]
  3. Innovation Foundation of Tianjin University [2013XJ-0005]
  4. National Basic Research Project of the MOST [2014CB932200]

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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(sp(2))-C(sp(2)) 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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