TY - JOUR
T1 - LiHMDS-Mediated Deprotonative Coupling of Toluenes with Ketones
AU - Shigeno, Masanori
AU - Kajima, Akihisa
AU - Toyama, Eito
AU - Korenaga, Toshinobu
AU - Yamakoshi, Hiroyuki
AU - Nozawa-Kumada, Kanako
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI Grant Number 19H03346 (Y.K.), the Environment Research and Technology Development Fund of the Environmental Restoration and Conservation Agency of Japan, Grant Number JPMEERF20202R02 (M.S.), JST, PRESTO Grant Number JPMJPR22N7 (M.S.), the New Energy and Industrial Technology Development Organization (NEDO) of Japan, Grant Number JPNP20004 (M.S.), Daicel Corporation (M.S.), and also Research Support Project for Life Science and Drug Discovery (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED under Grant Number JP22ama121040 (M.S. and K.N.K.).
Publisher Copyright:
© 2022 Wiley-VCH GmbH.
PY - 2022
Y1 - 2022
N2 - 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).
AB - 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).
KW - amide-base
KW - deprotonative coupling
KW - ketones
KW - olefination
KW - toluenes
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U2 - 10.1002/chem.202203549
DO - 10.1002/chem.202203549
M3 - Article
AN - SCOPUS:85147748200
SN - 0947-6539
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
ER -