4.5 Article

Palladium-Catalyzed Regioselective C-H Acetoxylation of 2-Aryloxypyridines with 2-Pyridyloxy as a Removable Directing Group

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 18, Pages 3113-3118

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600508

Keywords

Synthetic methods; Homogeneous catalysis; C-H activation; Palladium; Regioselectivity

Funding

  1. National Natural Science Foundation of China (NSFC) [21302014]
  2. Jiangsu Province Key Laboratory of Fine Petrochemical Engineering [KF1304]
  3. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
  4. Changzhou University, Advanced Catalysis and Green Manufacturing Innovation Center

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A simple and regioselective palladium-catalyzed ortho-C(sp(2))-H acetoxylation of 2-aryloxypyridines with PhI(OAc)(2) as both the oxidant and acetate source has been developed. The mono- and di-acetoxylated products can be achieved by tuning the equivalents of PhI(OAc)(2) and the reaction temperature. A wide range of 2-aryloxypyridines is tolerated. Moreover, 2-pyridyloxyl and acetyl groups can be easily removed, which provides straightforward access to poly-substituted phenols.

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