Annulation cascade of aryl alkynes induced by alumina-mediated C-F bond activation

Abstract

Alumina-mediated C-F activation (AmCFA) is an established method to generate incipient phenyl cation (IPC) through polarization of C(aryl)-F bonds. Herein, it is reported that AmCFA can be used to induce intramolecular arylation of aryl alkynes containing one, two, and three triple bonds. During the reaction, a single formally eliminated hydrogen fluoride (HF) leads to the formation of two, three, and four C-C bonds, respectively. Thus, the transformation gives rapid access to π-extension and serves as an interesting example of solid-state rational domino annulation enabling the bottom-up construction of nanographenes.