Recent studies in our group discovered a method for generating the first example of a monometallic iron-based azametallacyclobutene. Isolation of this product established a [2+2] cycloaddition mechanism in alkyne carboamination to form β-alkynl enamines from organic azides. Changing to the methyl-substituted β-diketiminate ligand revealed the instability of the <i>N</i>-mesityl imide complex, <sup>Me,Dipp</sup>LFeNMes. However, coordination of the alkyne to the iron before addition of the azide allows access to the metallacycle. With the iron azametallacyclobutene, insertion of nitrile substrates takes place at the Fe-N bond to form a new C-N bond and generate an imidazole product, compared to exclusive metal-carbon insertion seen in group 4 analogs. Carbene-like reactivity is seen in the reaction of the iron metallacycle with isonitrile substrates, generating ketenimine products.

Investigation of ligand modification in the synthesis and reactivity of iron azametallacyclobutenes

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