LiHMDS‐Mediated Deprotonative Coupling of Toluenes with Ketones
Masanori Shigeno, Akihisa Kajima, Eito Toyama, Toshinobu Korenaga, Hiroyuki Yamakoshi, Kanako Nozawa‐Kumada, Yoshinori Kondo
Abstract
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, OCF 3 , 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).
Topics & Concepts
TolueneConjugateAmideArylChemistryHalogenLithium (medication)Medicinal chemistryBase (topology)Lithium amideCombinatorial chemistryCatalysisOrganic chemistryPsychologyMathematicsPsychiatryEnantioselective synthesisAlkylMathematical analysisCatalytic C–H Functionalization MethodsCoordination Chemistry and OrganometallicsAdvanced Synthetic Organic Chemistry