4.7 Article

Selective Palladium-Catalyzed C-F Activation/Carbon-Carbon Bond Formation of Polyfluoroaryl Oxazolines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 4, Pages 1798-1804

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo2023262

Keywords

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Funding

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

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A selective palladium-catalyzed Suzuki-Miyaura coupling reaction of polyfluorophenyl oxazolines through ortho C-F activation is described. It was found that reactions with DPPF as the ligand occurred much faster than those with other ligands. A variety of arylboronic acids including challenging functionalized arylboronic acids such as enolizable ketones, aldehyde, cyano, ester, and trifluoromethyl groups were tolerated with the reaction conditions.

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