One-step synthesis to polycyclic thianthrenes from unfunctionalized aromatics by thia-APEX reaction
Kou. P. Kawahara, Hideto Ito,* Kenichiro Itami*
Org. Chem. Front., 2023, 10, 1880–1889. Open Access. DOI: 10.1039/D2QO02058K
Organic Chemistry Frontiers Emerging Investigator Series, 2023.
Cover picture vol 10, No. 8.
In this paper, thia-APEX reactions affording π-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 the π-extended thianthrenes in 21–87% yield. The present thia-APEX reaction occurs with equimolar amounts of aromatic substrates and S-diimidated 1,2-arenedithiol and a catalytic amount of TfOH, which is advantageous in the efficient creation of novel π-extended thianthrenes. In addition, unique solid state packing structure and photophysical properties of synthesized π-extended thianthrenes were elucidated in this study.