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

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Abstract

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, β-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 (π-benzyl)ruthenium intermediate.

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

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Supplementary files

Article information


Submitted
23 Dec 2019
Accepted
10 Feb 2020
First published
10 Feb 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

K. Suzuki, H. Tsuji and M. Kawatsura, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09899B

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