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DBU-Mediated Isomerization/6-π Electro-Cyclization/Oxidation Cascade of Sulfonyl-Substituted Allenyl Ketones for the Construction of Hetero-1,3,5-Trisubstituted Benzene.

Lihong WangRuiyang MaJiuli XiaXimin LiuJiaqiong SunGuangfan ZhengQian Zhang
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2023)
1,3,5-tri-substituted benzene rings emerged with unique properties has widespread applications in materials, boosting the rapid development of their synthesis. Despite the significance, the direct construction of hetero-1,3,5-trisubstituted benzene core was far less-developed. Herein, we realized a DBU-mediated isomerization/6-π electro-cyclization/oxidative aromatization cascade of sulfonyl-substituted allenyl ketones under an air atmosphere (DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). This versatile protocol featured metal-free conditions, easy operation, and broad functional group tolerance provides a new avenue for the construction of hetero-1,3,5-tri-substituted benzene.
Keyphrases
  • visible light
  • molecular docking
  • randomized controlled trial
  • high speed
  • molecular dynamics simulations
  • mass spectrometry
  • hydrogen peroxide