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Synfacts 2011(5): 0541-0541  
DOI: 10.1055/s-0030-1259774
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Benzylic Metalation with a Mixed Metal Li/K-TMP Amide

Contributor(s): Paul Knochel, Thomas Kunz
P. Fleming, D. F. O’Shea*
University College Dublin, Ireland
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

In this work, a general procedure for the benzylic metalation of ortho-, meta-, and para-substituted toluenes is disclosed. The excellent selectivity can be explained by an anion migration from the kinetic to the benzylic site, which is facilitated by the mixed metal amide base generated from BuLi, KOt-Bu, and TMPH in situ.