In situ generation of organocalcium compounds for a calcium-based Grignard-type chemistry.

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.