One-step synthesis of polycyclic thianthrenes from unfunctionalized aromatics by thia-APEX reactions

In this paper, thia-APEX reactions affording pi-extended thianthrene derivatives from unfunctionalized aromatics are described. By utilizing S-diimidated 1,2-arenedithiols as benzene-1,2-dithiol dication synthons, new benzodithiine arms were fused to the unfunctionalized aromatic substrates in one step, affording pi-extended thianthrenes in 21-87% yields. The present thia-APEX reaction occurs with equimolar amounts of aromatic substrates and S-diimidated 1,2-arenedithiols and a catalytic amount of TfOH, which is advantageous for the efficient creation of novel pi-extended thianthrenes. In addition, the unique solid state packing structures and photophysical properties of the synthesized pi-extended thianthrenes were elucidated in this study.

Automated summary

This paper describes the synthesis of pi-extended thianthrene derivatives from unfunctionalized aromatics using thia-APEX reactions. The reaction involves the fusion of new benzodithiine arms to the aromatic substrates in one step, resulting in the formation of pi-extended thianthrenes with yields ranging from 21% to 87%. The reaction requires equimolar amounts of the aromatic substrates and S-diimidated 1,2-arenedithiols, along with a catalytic amount of TfOH, and the synthesized pi-extended thianthrenes were characterized for their solid state packing structures and photophysical properties.