Iodotrimethylsilane-Mediated Cross-Aldol Condensation: A Facile Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones

Abstract

A facile and efficient method for the preparation of a,a¢-bis(substituted benzylidene)cycloalkanones is described for the first time using iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide in acetonitrile. The reaction proceeds rapidly at room temperature, giving high yields of products.

Pyrrolidine-Mediated Direct Preparation of (E)-Monoarylidene Derivatives of Homo- and Heterocyclic Ketones with Various Aldehydes

“…In connection with a project in our laboratory, we required mono-2-arylidene derivatives of ketones, particularly of piperidone. The ideal choice in our case is to form the mono-2-arylidene structural unit via a ClaisenSchmidt condensation between the parent ketones and aryl aldehydes [16][17][18][19]. However, this method employs a relatively strong base such as a metal hydroxide or metal alkoxide, so it is often accompanied by side reactions and it offers narrow substrate diversity.…”

Iodine catalyzed synthesis of α,α'‐bis(substituted benzylidene)‐1‐carbethoxy‐4‐piperidone

“…To the best of our knowledge, this is one of the few examples [18,19] in which cross-Aldol condensation of ketones with aldehydes, is carried out at room temperature to give enones. We found that CH 3 CN is more effective solvent in terms of yields than other solvents tested such as CHCl 3 , THF and EtOH.…”

Synthesis and Fluorescence Properties of α,α′-Bis(substituted-benzylidene)cycloalkanones Catalyzed by 1-Methyl-3(2-(sulfooxy)ethyl)-1H-imidazol-3-ium Chloride

“…[5] Different complexes of metal(II) ions have also been used as catalysts, but the yields were less than 38%. [6] In other cases, Cp 2 TiPh 2 , [7] BOMPTO [bis(p-ehtoxyphenyl)telluroxide], [8] RuCl 3 , [9] SmI 3 , [10] Cp 2 ZrH 2 , [11] TiCl 3 (SO 3 CF 3 ), [12] KFÁAl 2 O 3 , [13] FeCl 3 , [14] BF 3 ÁOEt 2 , [15] InCl 3 , [16] TMSCl=NaI, [17] Yb(OTf) 3 , [18] I 2 [19] , TCT [20] , NaOAc=HOAc, [21] and NKC-9 (polymer-supported sulfonic acid) [22] have also been used to promote the reaction. However, these methods have some drawbacks such as use of costly catalysts and toxic reagents and special catalyst preparation.…”