Issue 47, 2008

Catalytic direct-type substitution reaction of α-alkylenolates: a Pd/Brønsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates

Abstract

A mild and efficient process for the direct-type catalytic allylation of sulfonylimidates has been developed; this reaction represents the first example of Brønsted base-catalysed, in situ generation and use of α-alkylenolates in substitution reactions; the success of this methodology stems from the tunable α-proton acidity and nucleophilicity of sulfonylimidates, which could be harnessed in the realization of a broader range of catalytic direct-type reactions using ester equivalents as nucleophiles.

Graphical abstract: Catalytic direct-type substitution reaction of α-alkylenolates: a Pd/Brønsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates

Supplementary files

Article information

Article type
Communication
Submitted
10 Sep 2008
Accepted
01 Oct 2008
First published
29 Oct 2008

Chem. Commun., 2008, 6354-6356

Catalytic direct-type substitution reaction of α-alkylenolates: a Pd/Brønsted base-catalysed approach to the decarboxylative allylation of sulfonylimidates

S. B. J. Kan, R. Matsubara, F. Berthiol and S. Kobayashi, Chem. Commun., 2008, 6354 DOI: 10.1039/B815845B

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