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Issue 22, 2015
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A general Pd-catalyzed α- and γ-benzylation of aldehydes for the formation of quaternary centers

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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

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Publication details

The article was received on 08 Apr 2015, accepted on 30 Apr 2015 and first published on 30 Apr 2015


Article type: Paper
DOI: 10.1039/C5OB00702J
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Org. Biomol. Chem., 2015,13, 6338-6343

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    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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