One-step synthesis of polycyclic thianthrenes from unfunctionalized aromatics by thia-APEX reactions
One-step synthesis of polycyclic thianthrenes from unfunctionalized aromatics by thia-APEX reactions
复制标题
硫杂-APEX 反应从未官能化芳烃一步合成多环噻蒽
DOI：
10.1039/d2qo02058k
复制
发表时间：
2023
影响因子：
5.4
通讯作者：
Kenichiro Itami
中科院分区：
文献类型：
--
作者：
Kou P. Kawahara;Hideto Ito;Kenichiro Itami
本文介绍了由未官能化的芳烃通过thia-APEX反应合成π-扩展噻蒽衍生物的方法。通过利用S-二酰亚胺化的1，2-芳烃二硫醇作为苯-1，2-二硫醇二价阳离子，一步将新的苯并二噻二烯臂与未官能化的芳族底物稠合，以21-87%的产率得到π-延伸的噻蒽。本发明的thia-APEX反应在等摩尔量的芳族底物和S-二酰亚胺化的1，2-芳烃二硫醇以及催化量的TfOH的情况下发生，这有利于有效地产生新型π-延伸的噻蒽。此外，本研究还阐明了所合成的π-扩展噻蒽的独特固态堆积结构和物理化学性质。
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 π-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 π-extended thianthrenes. In addition, the unique solid state packing structures and photophysical properties of the synthesized π-extended thianthrenes were elucidated in this study.