Simple Lithiation of α,ω-Dihaloalkanes

Significance

The bis-organometallic compounds of type Met(CH₂)_nMet are very interesting for synthetic organic chemistry, as they allow the simultaneous introduction of two electrophilic moieties into a molecule. So far, not many examples of such compounds are known due to their instability and the problems connected with their synthesis. The authors investigated the preparation and reactions of α,ω-dilithioalkyls and showed that such compounds, while highly unstable, can sometimes be efficiently trapped with carbonyl electrophiles under Barbier conditions. This method can be conveniently used, for example, for the synthesis of linear diols and their derivatives.