Issue 22, 2015

A general Pd-catalyzed α- and γ-benzylation of aldehydes for the formation of quaternary centers

Abstract

A palladium-catalyzed benzylation of α-branched aldehydes has been developed using benzyl methyl carbonates. The method gives access to congested quaternary centers in the vicinity of one of the most sensitive carbonyl functionalities and displays unprecedented generality with respect to both coupling partners. Evidence for the direct involvement of a Pd-η3-benzyl intermediate is provided. Extension of this strategy to the γ-benzylation of α,β-unsaturated aldehydes is further demonstrated.

Graphical abstract: A general Pd-catalyzed α- and γ-benzylation of aldehydes for the formation of quaternary centers

Supplementary files

Article information

Article type
Paper
Submitted
08 Apr 2015
Accepted
30 Apr 2015
First published
30 Apr 2015

Org. Biomol. Chem., 2015,13, 6338-6343

Author version available

A general Pd-catalyzed α- and γ-benzylation of aldehydes for the formation of quaternary centers

I. Franzoni, L. Guénée and C. Mazet, Org. Biomol. Chem., 2015, 13, 6338 DOI: 10.1039/C5OB00702J

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