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

4 Citations (Scopus)

Abstract

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
Article numbere202203549
JournalChemistry - A European Journal
Volume29
Issue number15
DOIs
Publication statusPublished - 2023 Mar 13

Keywords

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

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