Recent progress in the chemistry of heavy aromatics

The aromaticity and synthetic application of heavy benzenes, i.e., benzenes containing a heavier Group 14 element (Si, Ge, Sn, and Pb) in place of skeletal carbon, have been the targets of many theoretical and synthetic studies. Although the introduction of a sterically demanding substituent enabled us to synthesize and isolate heavy aromatic species as a stable compound by suppressing their high reactivity and tendency to polymerize, the existence of a protection group is an obstruction to the development of functional materials based on heavy aromatics. This review will delineate the most recent topics in the chemistry of heavy aromatics, i.e., the chemistry of metallabenzenyl anions, which are the heavier Group 14 element analogs of phenyl anions stabilized by taking advantage of charge repulsion instead of steric protection.

Automated summary

The aromaticity and synthetic application of heavy benzenes, which are benzenes containing heavier Group 14 elements, have been extensively studied. This review focuses on the chemistry of metallabenzenyl anions, which are heavy analogs of phenyl anions stabilized by charge repulsion instead of steric protection.