4.7 Article

Pd-Catalyzed Substitution of the OH Group of Nonderivatized Allylic Alcohols by Phenols

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 7, Pages 4099-4104

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b03274

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Funding

  1. Swedish Research Council (Formas)
  2. Stiftelsen Olle Engkvist Byggmastare

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Nonactivated phenols have been employed as nucleophiles in the allylation of nonderivatized allylic alcohols to generate allylated phenolic ethers with water as the only byproduct. A Pd[BiPhePhos] catalyst was found to be reactive to give the O-allylated phenols in good to excellent yields in the presence of molecular sieves. The reactions are chemo-selective in which the kinetically favored O-allylated products are formed exclusively over the thermodynamically favored C-allylated products.

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