81206-69-1Relevant academic research and scientific papers
CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones
Jin, Xiongjie,Mizuno, Noritaka,Takei, Daisuke,Yabe, Tomohiro,Yamaguchi, Kazuya,Yatabe, Takafumi
, p. 5057 - 5063 (2020/05/27)
Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.
Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones
Diao, Tianning,Stahl, Shannon S.
supporting information; experimental part, p. 14566 - 14569 (2011/10/17)
α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)2(TFA)2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.
Diels-Alder Reactions of (Trifluoromethyl)ethene and (Trifluoromethyl)styrenes with Functionalized Butadiens
Ojima, Iwao,Yatabe, Momoko,Fuchikami, Takamasa
, p. 2051 - 2055 (2007/10/02)
The-Alder reactions of (trifluoromethyl)ethene (1) with 2-(trimethylsiloxy)buta-1,3-diene (2), 2--1,3-butadiene (4), and 1-methoxy-3-(trimethylsiloxy)buta-1,3-diene (6) were carried out to give the corresponding cycloadducts in 17-38percent yields.It was found that the former two cycloadducts were a mixture of para (major) and meta (minor) isomers, while the latter was the para isomer exlusively.Similary, β-(trifluoromethyl)-4-(methoxycarbonyl)styrene (9) and β-(trifluoromethyl)-4-nitrostyrene (10) were allowed to react with 4 and 6, giving the corresponding cycloadducts in 56-90percent yields.The regioselectivity of the reaction on using 6 as the diene turned out to be extremely high, leading to the formation of only one regioisomer.The substituent effect of the trifluoromethyl group in the Diels-Alder reaction in terms of regioselectivity is discussed.
