27798-41-0Relevant articles and documents
Benzylic aroylation of toluenes with unactivated tertiary benzamides promoted by directed ortho-lithiation
Bao, Can-Can,Luo, Yan-Long,Du, Hui-Zhen,Guan, Bing-Tao
, p. 1349 - 1354 (2021/07/12)
The deprotonative functionalization of toluenes, for their weak acidity, generally needs strong bases, thus leading to the requirement of harsh conditions and the generation of by-products. Direct nucleophilic acyl substitution reaction of amides with organometallic reagents could provide an ideal solution for ketone synthesis. However, the inert amides and highly reactive organometallic reagents bring great challenges for an efficient and selective synthetic approach. Herein, we reported an lithium diisopropylamide (LDA)-promoted benzylic aroylation of toluenes with unactivated tertiary benzamides, providing a direct and efficient synthesis of various aryl benzyl ketones. This process features a kinetic deprotonative functionalization of toluenes with a readily available base LDA. Mechanism studies revealed that the directed ortho-lithiation of the tertiary benzamide with LDA promoted the benzylic kinetic deprotonation of toluene and triggered the nucleophilic acyl substitution reaction with the amide. [Figure not available: see fulltext.].
Exploiting Aryl Mesylates and Tosylates in Catalytic Mono-α-arylation of Aryl- and Heteroarylketones
Fu, Wai Chung,So, Chau Ming,Yuen, On Ying,Lee, Irene Toi Chuk,Kwong, Fuk Yee
supporting information, p. 1872 - 1875 (2016/05/19)
The first general palladium catalyst for the catalytic mono-α-arylation of aryl- and heteroarylketones with aryl mesylates and tosylates is described. The newly developed indolyl-derived phosphine ligand L7 has been identified to promote this reaction eff
Palladium-catalyzed carbonylative suzuki coupling of benzyl halides with potassium aryltrifluoroborates in aqueous media
Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
experimental part, p. 788 - 792 (2011/05/15)
A general palladium-catalyzed carbonylative cross-coupling reaction of benzyl chlorides with potassium aryltrifluoroborates in water has been developed. Applying this improved methodology 16 different 1,2-diarylethanones have been synthesized in 40-89% yield. Copyright