<p>Skeletal reshaping between aromatic frameworks remains challenging. The rearrangements between azulene and naphthalene structures are some of the only examples to date. Metallaaromatics, an important class of aromatic compounds, attract broad attention for their fascinating structures and diverse reactivities. Herein, we report the reshaping of cyclopropametallaindole to metallaquinolinium, demonstrating both aromaticity and structure switching. The proposed electrophilic addition and elimination mechanism has been investigated by radical trapping experiment and theoretical study. This transformation achieves both the aromaticity and structure switching of a metallacycle, and demonstrates a new synthetic route for metallaaromatics.</p>