4.8 Article

Copper-Mediated Aerobic Fluoroalkylation of Arylboronic Acids with Fluoroalkyl Iodides at Room Temperature

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 15, Pages 6548-6551

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja301705z

Keywords

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Funding

  1. National Basic Research Program of China [2012CB821600, 2010CB126103]
  2. Special Fund for Agro-scientific Research in the Public Interest [201103007]
  3. National Key Technologies RD Program [2011BAE06B05]
  4. Shanghai Scientific Research Program [10XD1405200]
  5. National Natural Science Foundation of China [21032006]
  6. Shanghai Pujiang Program [11PJ1412200]
  7. SIOC

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A Cu-mediated ligandless aerobic fluoroalkylation of arylboronic acids under mild conditions is described for the first time. The reaction tolerates a wide range of functional groups, allowing for further transformation. Mechanistic studies suggest that [RfCu] is the active Cu species that forms the desired perfluoroalkylarenes and that [RfCu] is generated from [PhCu] by either an oxidative addition/reductive elimination mechanism or nucleophilic substitution via a halogen ate intermediate.

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