LiHMDS-Mediated Deprotonative Coupling of Toluenes with Ketones

Masanori Shigeno, Akihisa Kajima, Eito Toyama, Toshinobu Korenaga, Hiroyuki Yamakoshi, Kanako Nozawa-Kumada, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review


We demonstrate that lithium hexamethyldisilazide (LiHMDS) acts as an effective base for deprotonative coupling reactions of toluenes with ketones to afford stilbenes. Various functionalities (halogen, OCF3, amide, Me, aryl, alkenyl, alkynyl, SMe, and SPh) are allowed on the toluenes. Notably, this system proved successful with low-reactive toluenes bearing a large pKa value compared to that of the conjugate acid of LiHMDS (hexamethyldisilazane, 25.8, THF), as demonstrated by 4-phenyltoluene (38.57, THF) and toluene itself (∼43, DMSO).

Original languageEnglish
JournalChemistry - A European Journal
Publication statusAccepted/In press - 2022


  • amide-base
  • deprotonative coupling
  • ketones
  • olefination
  • toluenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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