4.7 Article

Ruthenium-catalyzed benzylic substitution of benzyl esters with stabilized carbon nucleophiles

Journal

CHEMICAL COMMUNICATIONS
Volume 56, Issue 22, Pages 3273-3276

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc09899b

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Funding

  1. Research Grant of Institute of Natural Sciences at Nihon University
  2. Japan Society for the Promotion of Science [17K05794]
  3. Grants-in-Aid for Scientific Research [17K05794] Funding Source: KAKEN

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We have accomplished the ruthenium-catalyzed benzylic substitution of benzyl esters with a stabilized carbon nucleophile. A [Cp*RuCl2](2)/picolinic acid catalyst system promoted the reaction of 2-naphthylmethyl-2,3,4,5,6-pentafluorobenzoates with a series of stabilized carbon nucleophiles such as malonates, beta-ketoesters, and diketones to give the corresponding benzylic alkylation products in moderate to high yields. We proposed a plausible reaction mechanism that could involve a (pi-benzyl)ruthenium intermediate.

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