37032-34-1Relevant academic research and scientific papers
Double Enzyme-Catalyzed One-Pot Synthesis of Enantiocomplementary Vicinal Fluoro Alcohols
Fan, Jiajie,Lin, Xianfu,Peng, Yongzhen,Wang, Anlin,Wu, Qi,Xu, Jian,Xu, Weihua,Yu, Huilei
supporting information, (2020/07/24)
A double-enzyme-catalyzed strategy for the synthesis of enantiocomplementary vicinal fluoro alcohols through a one-pot, three-step process including lipase-catalyzed hydrolysis, spontaneous decarboxylative fluorination, and subsequent ketoreductase-catalyzed reduction was developed. With this approach, β-ketonic esters were converted to the corresponding vicinal fluoro alcohols with high isolated yields (up to 92percent) and stereoselectivities (up to 99percent). This new cascade process addresses some issues in comparison with traditional methods such as environmentally hazardous reaction conditions and low stereoselectivity outcome.
Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo
Dan, Wen-Jia,Tuong, Thi-Mai-Luong,Wang, Da-Cheng,Li, Ding,Zhang, An-Ling,Gao, Jin-Ming
, p. 2861 - 2864 (2018/07/25)
A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.
Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation
Zhang, Rui,Ni, Chuanfa,He, Zhengbiao,Hu, Jinbo
, p. 166 - 172 (2017/09/18)
Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of β-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords α-fluoroketones with a broad scope. Both electron-rich and electron-deficient α-non-substituted β-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.
Α - fluoro acetophenone derivative
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Paragraph 0029; 0030, (2018/08/28)
PROBLEM TO BE SOLVED: To provide a new production method of an α-fluoroacetophenone derivative by a simple one-step fluorination reaction with an acetophenone derivative under a mild condition.SOLUTION: An acetophenone derivative represented by formula (I) is reacted with a hydrogen fluoride/amine complex in the presence of a hypervalent iodine compound, (in the formula, a ring A indicates an aromatic ring of 1-3 members; Rindicates a hydrogen atom or an aromatic ring of 1-3 members that may be substituted; Rindicates a hydrogen atom or an alkyl group of 1-6 carbons; and Rindicates a hydrogen atom, an alkyl group of 1-6 carbons, an alkoxy group of 1-6 carbons or a halogen atom). The H part in formula (I) is substituted and fluorinated.
Palladium-catalyzed direct mono-α-arylation of α-fluoroketones with aryl halides or phenyl triflate
Zhou, Jun,Fang, Xiang,Shao, Tongle,Yang, Xueyan,Wu, Fanhong
, p. 54 - 62 (2016/10/05)
A palladium catalyzed Negishi-type α-arylation of α-fluoroketones with electron-rich and electron-deficient aryl halides or phenyl triflate has been developed. This direct mono-α-arylation method generate a variety of ternary α-aryl-α-monofluoroketones easily in good to excellent yields using XPhos as ligand and Cs2CO3as mild base.
Fluorination of α-bromomethyl aryl ketones with fluorohydrogenate-based ionic liquids
Singh, Rajendra P.,Martin, Jerry L.
, p. 7 - 10 (2015/11/25)
Fluorination of α-bromomethyl aryl ketones using fluorohydrogenate-based ionic liquids as fluorinating reagent is described. Reaction of various α-bromomethyl aryl ketones (1a-g) with fluorohydrogenate-based ionic liquids such as EMIMF·(HF)2.3, PYR13F·(HF)2.3 or PYR14F·(HF)2.3 as a fluoride ion source in anhydrous THF led to the formation of the corresponding α-fluoromethyl aryl ketones (2a-g) in very good yield. Compared to alternative fluorinating agents for this reaction, fluorohydrogenate-based ionic liquids are safer to handle and have the potential to be less expensive and more selective.
Synthesis of α-Fluoroketones by Insertion of HF into a Gold Carbene
Zeng, Xiaojun,Liu, Shiwen,Shi, Zhenyu,Liu, Guangchang,Xu, Bo
supporting information, p. 10032 - 10036 (2016/08/16)
Reported is an efficient synthesis of α-fluoroketones by insertion of hydrogen fluoride (HF) into the gold carbene intermediate, generated from a cationic gold catalyzed addition of N-oxides to alkynes. This method results in excellent chemical yields for a wide range of alkyne substrates and demonstrates good functional-group tolerance.
A Practical Synthesis of α-Fluoroketones in Aqueous Media by Decarboxylative Fluorination of β-Ketoacids
Li, Jian,Li, Yin-Long,Jin, Nan,Ma, Ai-Lun,Huang, Ya-Nan,Deng, Jun
supporting information, p. 2474 - 2478 (2015/08/18)
A practical and novel process for the decarboxylative fluorination of β-ketoacids in water in the presence of phase transfer catalyst has been developed, affording a series of α-fluoroketones in good to excellent yields. Furthermore, a preliminary investigation for the catalytic asymmetric transformation was performed and a proposed mechanistic pathway for this catalytic process was proposed.
One-Pot Synthesis of α-Fluoroketones and 3-Fluoro-2,4-diaryl-furans from Trifluoromethyl β-Diketones via Decarboxylation
Shao, Tongle,Fang, Xiang,Yang, Xueyan
supporting information, p. 1835 - 1840 (2015/08/06)
A facile and mild one-pot protocol via decarboxylation of trifluoromethyl β-diketones has been developed for the construction of α-fluoroketones and 3-fluoro-2,4-diarylfurans which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.
Hypervalent iodine-promoted α-fluorination of acetophenone derivatives with a triethylamine·hf complex
Kitamura, Tsugio,Muta, Kensuke,Muta, Kazutaka
, p. 5842 - 5846 (2014/07/08)
The direct fluorination reaction of acetophenone using iodosylarenes and TEA·5HF was conducted under mild conditions except for use of a HF reagent. The fluorination reaction was applied to acetophenone derivatives, acetonaphthones, benzyl phenyl ketone, propiophenone, butyrophenone, 1-indanone, and phenacyl chloride, giving selectively the corresponding α-fluoroketone derivatives in good yields.
