- A novel and convenient synthesis of (Z)-3,3,3-trifluoropropenyl alkyl ethers and CF3-substituted propyl acetals as versatile CF3-containing building blocks
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A novel and convenient preparation of (Z)-3,3,3-trifluoropropyl alkyl ethers and their further transformation into CF3-substituted propyl acetals is described.
- Hong, Feng,Hu, Chang-Ming
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- 2,3,3,3-Tetrafluoropropene (HFO-1234yf) as a CF3-Building Block: Synthesis of Enol Ethers and Vinyl Sulfides
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2,3,3,3-Tetrafluoropropene (HFO-1234yf) is an inexpensive and readily available fluorinated building block, owing to its growing use as a low global warming potential 4th generation refrigerant, but there have so far been few reported uses of this fluoroalkene in organic synthesis. Herein, we report our investigations into nucleophilic substitution reactions of HFO-1234yf with alkoxide and thiolate derivatives. The regiochemistry of these transformations varies with conditions and we propose these reactions proceed through addition–elimination with reversible formation of a carbanion intermediate. The regioselectivity is dictated by hard/soft nucleophile/electrophile control. This is supported by deuterium trapping of the proposed reactive intermediate. The effect of solvent and base choice was examined and the substrate scope for the synthesis of α-trifluoromethyl enol ethers was expanded.
- Murray, Ben J.,Ball, Ellis D.,Harsanyi, Antal,Sandford, Graham
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p. 7666 - 7672
(2019/12/24)
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- Atom-economical synthesis of 3,3,3-trifluoropropanal dialkyl acetals through Pd/C catalyzed acetalization of 3,3,3-trifluoropropene
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A facile and efficient procedure for one-step synthesis of 3,3,3-trifluoropropanal dialkyl acetals from readily available 3,3,3-trifluoropropene (TFP) has been developed. The catalyst can be recycled for 4 times without obvious deactivation. This process provides a novel and atom-economical synthetic strategy for the preparation of functional CF3-containing compounds.
- Kang, Jian-Ping,Lu, Ju-You,Li, Yang,Wang, Zhi-Xuan,Mao, Wei,Lu, Jian
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p. 39387 - 39391
(2016/06/01)
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- A 3, 3, 3-three fluorine third method of synthesizing acid methyl ester
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The invention discloses a method for synthesizing 3,3,3-trifluoro methyl propionate. The method comprises the following steps of: putting 3,3,3-trifluoropropene serving as a raw material, methyl alcohol, a Pd/C catalyst and a pro-oxidant in a reaction kettle, after introducing 3,3,3-trifluoropropene and oxygen gas, heating up to the temperature of 70-120 DEG C, reacting for 8-12 hours, cooling and filtering reacted liquid; and adding obtained filtrate, protonic acid and the pro-oxidant into a three-neck flask, heating up to the temperature of 60-80 DEG C, dropwise adding hydrogen peroxide, and reacting for 4-8 hours, thereby obtaining 3,3,3-trifluoro methyl propionate. The method has the advantages that the few synthesizing steps (only two steps) are carried out, the yield is high, and the after-treatment is simple.
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Paragraph 0031; 0032
(2017/04/04)
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- Convenient synthesis of 3,3,3-trifluoropropanoic acid by hydrolytic oxidation of 3,3,3-trifluoropropanal dimethyl acetal
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A convenient and efficient method for preparing 3,3,3-trifluoropropanoic acid (1) is reported. The starting material is 1-chloro-3,3,3-trifluoropropene (2) that can be easily transformed into 3,3,3-trifluoropropanal dimethyl acetal (4) on treatment with methanol and KOH followed by acid-catalyzed addition of methanol. Direct transformation of 4 into 1 was efficiently achieved with 30% aqueous hydrogen peroxide (4.0 equiv.) in the presence of FeCl3 (0.025 equiv.) and hydrochloric acid (0.5 equiv.).
- Komata, Takeo,Akiba, Shinya,Hosoi, Kenji,Ogura, Katsuyuki
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- Preparation of polyfluoroaldehydes and polyfluoroacetals
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A group of polyfluoroaldehydes represented by 3,3,3-trifluoropropanal can be formed with very good selectivity by reacting polyfluoroalkenes represented by 3,3,3-trifluoropropene with water in the presence of a source of divalent palladium. A group of polyfluoroacetals represented by 1,1-dialkoxy-3,3,3-trifluoropropane can be formed with very good selectivity by reacting the same polyfluoroalkenes with an alcohol in the presence of a source of divalent palladium.
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