347-80-8

Upstream product

• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 62-53-3 aniline 
• 79128-83-9 N-(4-(trifluoromethyl)benzylidene)aniline 
• 1173706-99-4 N-(2-iodophenyl)-4-(trifluoromethyl)benzamide 
• 106376-16-3 p-trifluoromethylbenzoic acid phenyl ester 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 201230-82-2 carbon monoxide 
• 455-13-0 4-Iodobenzotrifluoride 
• 17082-12-1 trans-azobenzene 
• 61062-55-3 2-phenyl-1-(4-(trifluoromethyl)phenyl)ethan-1-one 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 3300-51-4 p-Trifluoromethylbenzylamine 
• 66003-76-7 Diphenyliodonium triflate 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 

Downstream Products

• 21084-31-1 (4-(dimethylamino)phenyl)(4-(trifluoromethyl)phenyl)methanone 
• 6833-18-7 4-methyl-N-phenylbenzamide 
• 134384-31-9 2-(4-trifluoromethylphenyl)benzothiazole 
• 339094-67-6 N-cyclohexyl-4-(trifluoromethyl)benzamide 
• 1229610-06-3 4-phenyl-2-(4-(trifluoromethyl)phenyl)quinazoline 
• 785708-07-8 N-(4-bromophenyl)-4-(trifluoromethyl)benzamide 
• 1281681-07-9 3-(N-phenyl-4-trifluoromethylphenylacetimidoyl)-1-(3-pyridylmethyl)thiourea 
• 425366-01-4 N-phenyl-4-trifluoromethyl-benzimidic acid 4-cyano-phenyl ester 
• 425366-17-2 phenyl-(4-trifluoromethyl-phenylmethylidyne)-ammonium 

Relevant academic research and scientific papers

An oxidative rearrangement of C,N-diarylaldimines to formamides using sodium perborate

Treatment of C,N-diaryladium (5) with sodium tetrahydrate in triflouroacetic acid solution at 70-80° C results in an oxidative rearrangement to N,N-diarylformamides (6(Scheme 1). A mechanism involving the initial formation of 2,3-diaryloxaziridines is proposed (Scheme 2).

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions

N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.

Fe-mediated synthesis of: N -aryl amides from nitroarenes and acyl chlorides

Amides are prevalent in nature and valuable functional compounds in agrochemical, pharmaceutical, and materials industries. In this work, we developed a selective and mild method for the synthesis of N-aryl amides. Starting from commercially available nitroarenes and acyl halides, N-aryl amides with good yields can be obtained in water. Especially in the process of transformation, Fe dust is the only reductant and additive, and the reaction can be easily performed on a large scale.

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

Cu-catalyzed arylation of bromo-difluoro-acetamides by aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts: New entries to aromatic amides

We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2, 2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully introduced. A wide range of 2-bromo-2, 2-difluoroacetamides as either aliphatic or aromatic secondary or tertiary amides were also reactive under the developed conditions. The described synthetic protocols displayed excellent efficiency and were successfully utilized for the expeditious preparation of diverse aromatic amides in good-to-excellent yields. The reactions were scaled up to gram quantities.

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.