4743-74-2Relevant academic research and scientific papers
Diastereoselective cycloadditions of chiral homoallylic alcohols with benzonitrile oxide
Kociolek, Martin G.,Hongfa, Chayanant
, p. 1811 - 1813 (2003)
The first diastereoselective cycloaddition of a nitrile oxide with a homoallylic alcohol is discussed. The reaction of benzonitrile oxide with the magnesium alkoxides of chiral homoallylic alcohols has been shown to proceed with good diastereoselectivity, favoring the syn isomer of the resulting 2-isoxazoline.
Nitrogen-Doped Carbon-Incarcerated Zinc Electrodes as Heterogeneous Catalysts for Electrochemical Allylation of Carbonyl Compounds
Masuda, Ryusuke,Yasukawa, Tomohiro,Yamashita, Yasuhiro,Kobayashi, Shū
, p. 3453 - 3460 (2022/02/23)
Electrochemical allylation reactions of carbonyl compounds using cathodes prepared from nitrogen-doped carbon (NDC)-incarcerated zinc catalysts have been developed. A range of aldehydes and ketones afforded the desired allylic alcohols in high yields with 10 mol % zinc leaching, and the heterogeneous nature of the active species was suggested. Compared with bulk zinc electrodes, NDC-stabilized zinc nanoparticle species were compatible with a broader range of heteroaromatic substrates and enabled the use of an undivided cell.
Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds
Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong
, p. 2134 - 2141 (2021/09/29)
A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]
Indium-mediated allylation of carbonyl compounds in deep eutectic solvents
González-Gallardo, Nerea,Saavedra, Beatriz,Guillena, Gabriela,Ramón, Diego J.
, (2021/08/26)
This study describes, for the first time, the in situ generation of indium organometallic reagents in environmentally friendly deep eutectic solvents (DESs). The allylation process of different carbonyl compounds is achieved mediated by indium metal and u
A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions
Yin, JieXiang,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2347 - 2354 (2020/02/04)
A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not re
Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols
Lübbesmeyer, Maximilian,Mackay, Emily G.,Raycroft, Mark A. R.,Elfert, Jonas,Pratt, Derek A.,Studer, Armido
supporting information, p. 2609 - 2616 (2020/03/03)
The Cα-Cβ bond in homoallylic alcohols can be activated under basic conditions, qualifying these nonstrained acyclic systems as radical allylation reagents. This reactivity is exemplified by photoinitiated (with visible light and/or
MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
Fernandes, Rodney A.,Ramakrishna, Gujjula V.,Bethi, Venkati
, p. 6115 - 6125 (2020/10/27)
Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.
Spiro-dihydrobenzo-silole diphenol compounds, synthesis method and application thereof (by machine translation)
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Paragraph 0702-0712, (2020/06/17)
The invention discloses a spirodiclole diphenol compound as shown in a formula I as well as a synthesis method and application thereof. The method has the characteristics of simplicity and convenience in operation, easily available raw materials, mild rea
Copper(I) Diphosphine Bifluoride Complexes as Efficient Preactivated Catalysts for Nucleophilic Addition on Unsaturated Functional Groups
Rasson, Corentin,Riant, Olivier
supporting information, p. 835 - 840 (2020/02/13)
Herein we report the synthesis of a family of copper(I) diphosphine bifluoride complexes, their characterization, and their use as efficient preactivated catalysts for nucleophilic copper addition of pronucleophiles on unsaturations. Their use as mechanistic probes is also highlighted by the identification of two copper deuterides.
Copper-Impregnated Magnesium-Lanthanum Mixed Oxide: A Reusable Heterogeneous Catalyst for Allylation of Aldehydes and Ketones
Laha, Soumi,Likhar, Pravin R.,Pogula, Jaya,Sreedhar, B.
supporting information, (2020/02/11)
Copper-impregnated magnesium-lanthanum mixed oxide [Cu(II)/Mg?La] was used as catalyst in synthesis of homoallylic alcohols from aldehydes and ketones using allyltributylstannane as the allylating source. The present protocol provides a great application
