5764-85-2Relevant academic research and scientific papers
Thiourea-catalyzed nucleophilic addition of TMSCN and ketene silyl acetals to nitrones and aldehydes
Okino, Tomotaka,Hoashi, Yasutaka,Takemoto, Yoshiji
, p. 2817 - 2821 (2003)
The effect of hydrogen bonding between nitrones and urea derivatives in the nucleophilic addition reaction was examined. Thioureas bearing an electron-withdrawing group on an aromatic ring, behave like Lewis acid to promote the addition of TMSCN and keten
KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols
Li, Xinying,Mi, Tongge,Guo, Wenjing,Ruan, Zhongrui,Guo, Yu,Ma, Yan-Na,Chen, Xuenian
, p. 12776 - 12779 (2021/12/10)
Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters. This journal is
Photoinduced Oxidative Alkoxycarbonylation of Alkenes with Alkyl Formates
Tang, Wan-Ying,Chen, Ling,Zheng, Ming,Zhan, Le-Wu,Hou, Jing,Li, Bin-Dong
supporting information, p. 3939 - 3943 (2021/05/26)
A photoinduced oxidative alkoxycarbonylation of alkenes initiated by intermolecular addition of alkoxycarbonyl radicals has been demonstrated. Employing alkyl formates as alkoxycarbonyl radical sources, a range of α,β-unsaturated esters were obtained with good regioselectivity and E selectivity under ambient conditions.
Visible-Light-Driven, Metal-Free Divergent Difunctionalization of Alkenes Using Alkyl Formates
Zheng, Ming,Hou, Jing,Zhan, Le-Wu,Huang, Yan,Chen, Ling,Hua, Li-Li,Li, Yan,Tang, Wan-Ying,Li, Bin-Dong
, p. 542 - 553 (2021/01/14)
In recent decades, difunctionalization of alkenes has received considerable attention as an efficient and straightforward way to increase molecular complexity. However, examples of the difunctionalization of alkenes initiated by the intermolecular addition of alkoxycarbonyl radicals providing substituted alkanoates are still rare. Herein, we present the visible light-driven metal-free divergent difunctionalization of alkenes triggered by the intermolecular addition of alkoxycarbonyl radicals under ambient conditions. Employing alkyl formates as precursors of alkoxycarbonyl radicals and 4CzIPN as the photocatalyst, a variety of substituted alkanoates, including β-alkoxy, β-hydroxy, β-dimethoxymethoxy, and β-formyloxy alkanoates, could be facilely accessed with high functional group tolerance and high efficiency. Moreover, the mechanism study revealed that β-hydroxy alkanoates were generated by a selective decomposition of orthoformates promoted by the N-alkoxyazinium salt.
Synthesis method of beta-hydroxy ester compound
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Paragraph 0045-0085, (2020/07/12)
The invention belongs to the technical field of medicine and organic chemical synthesis, and discloses a synthesis method of a beta-hydroxy ester compound. An aldehyde compound and an iodo-acetate compound are used as raw materials; manganese powder is adopted as an accelerant, metal nickel salt is adopted as a catalyst and an organic solvent is adopted as a reaction medium, an organic protonic acid is added and stirred and reacted under inert gas protection, the reaction system is cooled to room temperature after the reaction is finished, vacuum distillation and concentration are performed toobtain a crude product, and column chromatography purification is performed to obtain the beta-hydroxy ester compound. The synthesis method is safe and simple to operate, raw materials are easy to obtain, the price is low, the reaction efficiency is high, and the yield can reach 90% or above and even reach 98%; the method is good in functional group adaptability, wide in substrate adaptability, environmentally friendly, beneficial to industrial production and wide in application in medicine and organic synthesis.
Nickel-catalyzed deoxygenation of oxiranes: Conversion of epoxides to alkenes
Mori, Takamichi,Takeuchi, Yoshihito,Hojo, Makoto
, (2020/01/24)
Deoxygenation of epoxides takes place under the catalysis of nickel in the presence of diethylzinc as a deoxygenation agent to yield alkenes. Epoxides with a wide variety of substitution patterns are deoxygenated in this catalytic system to give terminal, 1,1-disubstituted, 1,2-disubstituted, trisubstituted, and tetrasubstituted alkenes in high yields. Reactions of 1,2-disubstituted epoxides we examined proceeded in an E-stereoselective manner. High compatibility with other functional groups through this transformation was also observed.
One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents
Downey, C. Wade,Dixon, Grant J.,Ingersoll, Jared A.,Fuller, Claire N.,MacCormac, Kenneth W.,Takashima, Anna,Sediqui, Rohina
, (2019/10/14)
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.
Iron(0)-Mediated Reformatsky Reaction for the Synthesis of β-Hydroxyl Carbonyl Compounds
Liu, Xuan-Yu,Li, Xiang-Rui,Zhang, Chen,Chu, Xue-Qiang,Rao, Weidong,Loh, Teck-Peng,Shen, Zhi-Liang
supporting information, p. 5873 - 5878 (2019/08/20)
An efficient, economical, and practical Reformatsky reaction of α-halo carbonyl compounds with aldehydes/ketones by using cheap and commercial iron(0) powder as reaction mediator is developed. The reactions proceeded effectively in the presence of a catalytic amount of iodine (20 mol %) to afford the synthetically useful β-hydroxyl carbonyl compounds in moderate to good yields.
A Ball-Milling-Enabled Reformatsky Reaction
Cao, Qun,Stark, Roderick T.,Fallis, Ian A.,Browne, Duncan L.
, p. 2554 - 2557 (2019/06/17)
An operationally simple one-jar one-step mechanochemical Reformatsky reaction using in situ generated organozinc intermediates under neat grinding conditions has been developed. Notable features of this reaction protocol are that it requires no solvent, no inert gases, and no pre-activation of the bulk zinc source. The developed process is demonstrated to have good substrate scope (39–82 % yield) and is effective irrespective of the initial morphology of the zinc source.
Method for preparing β - hydroxyl carbonyl compound (by machine translation)
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Paragraph 0062-0066, (2019/10/01)
The present invention relates to a process for preparing β - hydroxycarbonyl compounds, which mainly provides a process for the reaction, using inexpensive commercial iron powder-mediated α -halocarbonyl compounds with aldehydes/ketones, to provide the corresponding β - hydroxycarbonyl compound . the present invention relates to a method. The process is good, has wide functional group tolerance and good compatibility. (by machine translation)
