Direct benzylic metalation of a phenethylamine derivative: potassium as the key to both generation and stabilization of a labile anion.

Christian Unkelbach, Hannah S Rosenbaum, Carsten Strohmann

Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany.

Chemical communications (Cambridge, England) 2012 Nov 7

filter terms:

t-BuLi-t-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.

Citation

Christian Unkelbach, Hannah S Rosenbaum, Carsten Strohmann. Direct benzylic metalation of a phenethylamine derivative: potassium as the key to both generation and stabilization of a labile anion. Chemical communications (Cambridge, England). 2012 Nov 7;48(86):10612-4