73471-97-3

Usage

InChI:InChI=1/C12H13F3O/c1-11(2,3)9-6-4-8(5-7-9)10(16)12(13,14)15/h4-7H,1-3H3

Upstream product

• 253185-03-4 tert-butylbenzene 
• 96254-05-6 2-(trifluoroacetyloxy)pyridine 
• 407-25-0 trifluoroacetic anhydride 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 63488-10-8 4-tert-butylmagnesium bromide 
• 383-63-1 ethyl trifluoroacetate, 
• 201230-82-2 carbon monoxide 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 16184-89-7 4'-bromo-2,2,2-trifluoroacetophenone 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 75-46-7 trifluoromethan 
• 26537-19-9 methyl 4-tert-butylbenzoate 
• 123324-71-0 p-tert-butylphenylboronic acid 

Downstream Products

• 173681-58-8 1-(4-tert-Butyl-2-iodo-phenyl)-2,2,2-trifluoro-ethanone 
• 1050445-54-9 2-(4-t-butylphenyl)-1,1,1-trifluorobutan-2-ol 
• 887616-50-4 (E)-4-(4-t-butylphenyl)-5,5,5-trifluoro-3-penten-2-yl mesylate 
• 887616-44-6 (E)-4-(4-t-butylphenyl)-5,5,5-trifluoro-3-penten-2-ol 

Relevant academic research and scientific papers

Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones

The trifluoromethylation of benzoic acids with TMSCF3 was achieved through nucleophilic substitution with the use of anhydrides as an in situ activating reagent. Under the reaction conditions, a wide range of carboxylic acids including the bioactive ones worked well, thus providing a facile and efficient method for preparing aryl trifluoromethyl ketones from the readily available starting materials.

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

A straightforward method that enables the formation of biologically attractive trifluoromethyl ketones from readily available methyl esters using the potent greenhouse gas fluoroform (HCF3, HFC-23) was developed. The combination of fluoroform and KHMDS in triglyme at ?40 °C was effective for this transformation, with good yields as high as 92%. Substrate scope of the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated methyl esters. This study presents a straightforward trifluoromethylation process of various methyl esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores under the reaction conditions was also explored.

Decarboxylative and Deaminative Alkylation of Difluoroenoxysilanes via Photoredox Catalysis: A General Method for Site-Selective Synthesis of Difluoroalkylated Alkanes

A general method for site-selective difluoroalkylation of alkyl carboxylic redox esters with difluoroenoxysilanes through photoredox-catalyzed decarboxylative reaction has been developed. The reaction can also be extended to aliphatic amine derived pyridinium salts. This method has the advantages of high efficiency, mild reaction conditions, and broad substrate scope, including primary, secondary, and sterically hindered tertiaryl alkyl substrates, providing a general and practical route for applications in organic synthesis and pharmaceutical studies.

N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application

The invention belongs to the technical field of medical chemical engineering intermediates and related chemistry, and relates to N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application. The N-phenyl-N-p-toluenesulfonyl trifluoroacetamide is taken as a trifluoroacetylation reagent, reacts with an arylboronic acid derivative in an anhydrous organic solvent under the action of a metalcatalyst, a ligand and an alkali, and is efficiently and highly selectively converted into a trifluoroacetophenone compound. According to a synthesis method of the trifluoroacetophenone compound, involved in the invention, reaction steps are few; the NTFTS which is stable in use, easy to store, cheap and easy to get is taken as a trifluoroacetyl source; environmental friendliness is realized; reaction conditions are mild; operation is easy; a high-yield and high-selectivity target product is obtained and has relatively good industrial production value and practical application value. The trifluoroacetophenone compound synthesized by utilizing the method can be further subjected to a functionalization reaction, and can be widely applied to the synthetic fields of medicine, pesticide, bioactive molecules, functional material molecules and the like.

Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer

The construction of quaternary centers is a common challenge in the synthesis of complex materials and natural products. Current cross-coupling strategies that can be generalized for setting these centers are sparse and, when known, are typically predicated on the use of reactive organometallic reagents. To address this shortcoming a new, photoredox-Ni dual catalytic strategy for the cross-coupling of tertiary organoboron reagents with aryl halides is reported. In addition to details on the cross-coupling scope and limitations, full screening efforts and mechanistic experiments are communicated.

Palladium-catalyzed carbonylative coupling of aryl iodides with an organocopper reagent: A straightforward procedure for the synthesis of aryl trifluoromethyl ketones

A palladium-catalyzed carbonylative coupling of aryl iodides with a (trifluoromethyl)copper reagent has been developed. A wide range of substrates have been transformed into their corresponding trifluoromethyl ketones in good to excellent yields under mild conditions with high efficiency and excellent functional-group compatibility. Preliminary mechanistic investigations suggest that the transmetallation of an acylpalladium intermediate with the (trifluoromethyl)copper reagent seems to be involved in the catalytic cycle. Notably, this report represents one of the few studies on carbonylative coupling with organocopper reagents.

A Weinreb amide approach to the synthesis of trifluoromethylketones

A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.

Palladium-catalyzed regio- and stereoselective formate reduction of fluorine-containing allylic mesylates. A new entry for the construction of a tertiary carbon attached with a fluoroalkyl group

The regioselective palladium-catalyzed formate reduction of γ-fluoroalkylated allylic esters is described. Reduction of the allylic esters under the influence of palladium with a monodentate phosphine ligand proceeded preferentially at the γ position, the corresponding reduction products with a fluoroalkyl group at the tertiary carbon being afforded in high yields. When the chiral allylic ester was employed, complete chirality transfer was observed, leading to the optically active materials in high yields.

A simple method for the preparation of aryl trifluoromethyl ketones

4-Dimethylamino-1-trifluoroacetylpyridinium trifluoroacetate (2) is an effective, easy to handle and stable trifluoroacetylation agent. Aryl trifluormethyl ketones 4 are obtained in good yields by reaction of 2 with aromatic compounds 3 in the presence of aluminum chloride.