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Issue 86, 2012
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Direct benzylic metalation of a phenethylamine derivative: potassium as the key to both generation and stabilization of a “labile anion”

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Abstract

t-BuLit-BuOK selectively metalates the benzylic position of 2-phenylethyldimethylamine under mild conditions without occurrence of β-elimination in the resulting metalated species. Theoretical and structural studies indicate that potassium is crucial for both the lowering of the barrier of the initial deprotonation step and the stabilization of the labile anion.

Graphical abstract: Direct benzylic metalation of a phenethylamine derivative: potassium as the key to both generation and stabilization of a “labile anion”

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Publication details

The article was received on 14 Aug 2012, accepted on 07 Sep 2012 and first published on 07 Sep 2012


Article type: Communication
DOI: 10.1039/C2CC35888C
Citation: Chem. Commun., 2012,48, 10612-10614
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    Direct benzylic metalation of a phenethylamine derivative: potassium as the key to both generation and stabilization of a “labile anion”

    C. Unkelbach, H. S. Rosenbaum and C. Strohmann, Chem. Commun., 2012, 48, 10612
    DOI: 10.1039/C2CC35888C

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