Synthesis of Ferrocenyl Alkyne–Cu(I) π‑Complexes via Copper-Promoted 8‑Aminoquinoline-Directed C–H Bond Alkynylations

A highly monoselective synthesis of ferrocenyl alkynes was achieved via Cu-promoted ferrocene C­(sp²)–H bond activations. The reaction employs an 8-aminoquinoline group as the directing group and terminal alkynes as the alkyne source. It was found the alkynylation products actually complex with the in situ generated Cu­(I) ions to give robust and stable alkyne π-copper complexes. In addition, these alkyne π-copper complexes could be freed of the copper ions to give various ferrocenyl alkynes in almost quantitative yields. The test results also showed that the alkyne π-copper complexes could be reformed from the free alkynes upon treating them with Cu­(I) salts.