Synthesis of 1,2-dicyanoferrocene by cyanation reactions

Abstract

We report two synthetic pathways for the preparation of 1,2-dicyanoferrocene, in a search for new dinitrile-based precursors that could be useful in the synthesis of metallocene-containing azaporphyrins, as well as in catalysis. Both procedures include cyanation reactions as the key steps. Magnesiation of cyanoferrocene, followed by reaction with electrophilic tosyl cyanide, affords the target compound in only two synthetic steps from ferrocene. In addition, 1,2-dicyanoferrocene can be prepared by a three step procedure, which implies a twofold cyanation of 1,2-dibromoferrocene, using Zn(CN)[Formula: see text], in a biphasic medium and in the presence of bulky [Formula: see text]-BuXPhos-Pd-G3.