LiHMDS‐Mediated Deprotonative Coupling of Toluenes with Ketones

Autor: Masanori Shigeno, Akihisa Kajima, Eito Toyama, Toshinobu Korenaga, Hiroyuki Yamakoshi, Kanako Nozawa‐Kumada, Yoshinori Kondo
Rok vydání: 2023
Předmět:
Zdroj: Chemistry – A European Journal. 29
ISSN: 1521-3765
0947-6539
DOI: 10.1002/chem.202203549
Popis: 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).
Databáze: OpenAIRE
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