128271-44-3

Upstream product

• 88486-65-1 3,3,3-trifluoro-2-methyl-1-phenylpropan-1-ol 
• 129946-88-9 Umemoto's reagent 
• 93-55-0 1-phenyl-propan-1-one 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 591-51-5 phenyllithium 
• 2314-97-8 iodotrifluoromethane 
• 637-50-3 1-phenylpropene 
• 2926-29-6 Langlois reagent 
• 39623-95-5 1-phenylprop-1-enyl acetate 
• 887144-94-7 Togni's reagent II 
• 117984-78-8 triethyl((1-phenylprop-1-en-1-yl)oxy)silane 
• 873-66-5 1-propenylbenzene 

Downstream Products

• 88486-65-1 (1RS,2SR)-3,3,3-trifluoro-2-methyl-1-phenylpropan-1-ol 
• 88486-65-1 (1RS,2RS)-3,3,3-trifluoro-2-methyl-1-phenylpropan-1-ol 

Relevant academic research and scientific papers

Zn-mediated rhodium-catalyzed α-trifluoromethylation of ketones via silyl enol ethers

The treatment of silyl enol ethers of ketones with CF3-I and Et2Zn in the presence of RhCl(PPh3)3 in DME gave α-trifluoromethyl ketones in good yields. The reaction can be widely applicable to silyl enol ethers

Mild Electrophilic Trifluoromethylation of β-Ketoesters and Silyl Enol Ethers with 5-Trifluoro Methyldibenzothiophenium Tetrafluoroborate

Cyclic and acyclic β-ketoesters were efficiently trifluoromethylated with 5-trifluoromethyldibenzothiophenium tetrafluoroborate in the presence of a phase-transfer catalyst to afford the corresponding α-substituted α-trifluoromethyl β-ketoesters in good t

New Method for Trifluoromethylation of Enolate Anions and Applications to Regio-, Diastereo- and Enantioselective Trifluoromethylation

Assessment was made of the effectiveness of different boron Lewis acids in mediating the trifluoromethylation of reactive enolate anions with S- and Se-(trifluoromethyl)chalcogen salts.Treatment of potassium or lithium enolates derived in situ from carbonyl compounds or enol trimethylsilyl ethers with S-(trifluoromethyl)dibenzothiophenium triflate (1) in the presence of 2-phenyl-1,3,2-benzodioxaborole (4) produced trifluoromethylated carbonyl compounds in high yields.In this manner, various α-CF3 ketones, γ-CF3-α,β-unsaturated ketones, and an α-CF3 ester were synthesized.Perfluorooctylation was similarly conducted using S-(perfluorooctyl)dibenzothiophenium triflate and 4.Thus, a balance of the reactivity of the reactants was essential for these electrophilic perfluoroalkylations.The deprotonation of 2-methylcyclohexanone with KN(SiMe3)2 followed by trifluoromethylation gave the 6-trifluoromethylated product regioselectively.In the trifluoromethylation of potassium enolate 16 of 4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone, the use of bulky 2-mesitylphenanthro-1,3,2-dioxaborole (15) led to the diastereoselective formation of the thermodynamically less stable CF3-isomer 17β.For enantioselective trifluoromethylation, optically active (S)-4-phenyldinaphthodioxaborepin (19) and its 3,3'-diphenyl derivative 20 were synthesized.The trifluoromethylation of the potassium enolate of propiophenone with 1 in the presence of 20 afforded optically active α-CF3-propiophenone in 45percent ee yield.Thus, a new and versatile method for selective trifluoromethylation has been developed.

Rational Design and Development of Low-Price, Scalable, Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents

The development of two highly reactive electrophilic trifluoromethylating reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as a trifluoromethyl radical for a variety of trifluoromethylative transformations under visible light irradiation, including radical trifluoromethylation of electron-rich indoles and pyrroles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives. On the other hand, as a complimentary, under reductive coupling conditions, reagent 1j reacted with a variety of (hetero)aryl iodides for the formation of trifluoromethylated (hetero)arenes.

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

The electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.

On the reactivity of anodically generated trifluoromethyl radicals toward aryl alkynes in organic/aqueous media

An in-depth study of the reaction of electrochemically generated trifluoromethyl radicals with aryl alkynes in the presence of water is presented. The radicals are readily generated by anodic oxidation of sodium triflinate, an inexpensive and readily avai

Multicomponent Oxidative Trifluoromethylation of Alkynes with Photoredox Catalysis: Synthesis of α-Trifluoromethyl Ketones

The direct oxidative addition of CF3 and H2O to alkynes was achieved with photoredox catalysis to obtain α-trifluoromethyl ketones via rapid enol-keto tautomerization. The reaction exhibits high functional group tolerance and regioselectivity. Heterocycles of various sizes containing CF3 were synthesized from the α-CF3-substituted diketones obtained through the protocol, thereby demonstrating the versatile applicability of the method. Mechanistic studies of the reaction with isotopes provided insight into the reaction pathway.

Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α-Halo Carbonyl Compounds

Salt-free stereoselective synthesis of silyl enol ethers was achieved by treating α-halo carbonyl compounds with 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine. In this reaction, easily removable trimethylsilyl halides and 2,3,5,6-tetramethylpyrazine were generated as the reaction byproducts. Due to the inertness of the reaction byproducts, we found a one-pot transformation of the in situ generated silyl enol ethers into various α-functionalized carbonyls by reaction with Togni-II reagent or aldehydes.

Sunlight-driven trifluoromethylation of olefinic substrates by photoredox catalysis: A green organic process

The principles and utility of photoredox catalysis in organic synthesis are described. After a brief description of the features of the two types of catalytic photoredox processes following the reductive quenching cycle (RQC) and the oxidative quenching cycle (OQC), the discussion is focused on organic transformations based on OQC, in particular the trifluoromethylation of olefinic substrates with electrophilic trifluoromethylating reagents furnishing solvolytic addition products and substitution products. It is concluded that catalytic photoredox systems are green from the point of view of harmfulness, safety, and energy source (visible light, including sunlight). Future prospects of photoredox catalysis will be also discussed.

Manganese-Catalyzed Aerobic Oxytrifluoromethylation of Styrene Derivatives Using CF3SO2Na as the Trifluoromethyl Source

A mild and practical protocol for manganese-catalyzed aerobic oxytrifluoromethylation of olefinic bonds of styrene derivatives using CF3SO2Na (Langlois reagent) as the CF3 source is described. A distinguishing feature of this method is the generation of trifluoromethyl radicals from CF3SO2Na using the simple manganese salt/O2 system. The reaction proceeds under ambient conditions, free of added peroxide initiators, and provides moderate to good selectivities for alcohol versus ketone product.