Abstract
AbstractOrganolithium compounds can behave as reductants but never as oxidants in redox reactions. Reported herein is that 1,4‐dilithio‐1,3‐butadienes reacted with [Ni(cod)2] (cod=1,5‐cyclooctadiene) to deliver dilithionickeloles. Single‐crystal X‐ray structural analysis revealed a coplanar structure of dilithionickeloles with an averaging of bond lengths. XPS data confirmed the oxidation state of Ni in dilithionickeloles was Ni2+. 7Li NMR spectra of dilithionickeloles and theoretical calculations revealed a considerable aromatic character. In this redox reaction, the dilithio dianionic compounds behaved as formal oxidants, thus oxidizing Ni0 into Ni2+. These results demonstrated that organolithium compounds with π‐conjugation could be used as oxidants and could continue to accept extra electrons.
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