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Updated: Jun 17, 2025

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
In situ generation of organocalcium compounds for a calcium-based Grignard-type chemistry
Simon Sengupta1, Sven Krieck1, Matthias Westerhausen1
1Institute of Inorganic and Analytical Chemistry, Friedrich Schiller University Jena, Humboldtstraße 8, D-07743 Jena, Germany. m.we@uni-jena.de.
Abstract:
Organocalcium compounds are highly reactive reagents whereas the alkaline-earth metal itself is a weak reductant. This discrepancy hampered a straightforward development of an organocalcium chemistry. The in situ generation of the highly reactive organocalcium reagent and immediate metalation of a H-acidic compound (iGMM) or addition onto a polar π-system (iGAM) offers not only a loophole to organocalcium reagents but opens the entry to a rich organic chemistry of this non-toxic and globally abundant alkaline-earth metal, being competitive to the organolithium chemistry.
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