3360-56-3

Upstream product

• 4028-63-1 iodomesitylene 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 76-05-1 trifluoroacetic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 56-23-5 tetrachloromethane 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 2314-97-8 iodotrifluoromethane 
• 171364-84-4 2-(2,4,6-trimethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 1330002-63-5 C₁₅H₂₅N₃ 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1436389-43-3 2,2-difluoro-2-(2,4,6-trimethylphenyl)acetic acid ethyl ester 
• 1436389-32-0 2-(2,4,6-trimethylphenyl)-2,2-difluoroacetic acid 
• 93683-27-3 perfluoro-2,4-dimethyl-3-ethylpent-3-yl radical 
• 75-63-8 Bromotrifluoromethane 

Downstream Products

• 14679-13-1 2-(2,4,6-trimethylphenyl)propene 
• 3360-58-5 3,5-Dimethyl-4-trifluormethyl-benzoesaeure-azid 
• 42175-50-8 1,2,3,5-tetrakis(trifluoromethyl)benzene 
• 3360-57-4 3,5-Dimethyl-4-trifluormethyl-benzoesaeure 
• 42175-51-9 trifluoromethyltrimesic acid 

Relevant academic research and scientific papers

Photoinduced Trifluoromethylation of Arenes and Heteroarenes Catalyzed by High-Valent Nickel Complexes

We describe a series of air-stable NiIII complexes supported by a simple, robust naphthyridine-based ligand. Access to the high-valent oxidation state is enabled by the CF3 ligands on the nickel, while the naphthyridine exhibits either a monodentate or bidentate coordination mode that depends on the oxidation state and sterics, and enables facile aerobic oxidation of NiII to NiIII. These NiIII complexes act as efficient catalysts for photoinduced C(sp2)?H bond trifluoromethylation reactions of (hetero)arenes using versatile synthetic protocols. This blue LED light-mediated catalytic protocol proceeds via a radical pathway and demonstrates potential in the late-stage functionalization of drug analogs.

Electrophotocatalytic Undirected C?H Trifluoromethylations of (Het)Arenes

Electrophotochemistry has enabled arene C?H trifluoromethylation with the Langlois reagent CF3SO2Na under mild reaction conditions. The merger of electrosynthesis and photoredox catalysis provided a chemical oxidant-free approach for the generation of the CF3 radical. The electrophotochemistry was carried out in an operationally simple manner, setting the stage for challenging C?H trifluoromethylations of unactivated arenes and heteroarenes. The robust nature of the electrophotochemical manifold was reflected by a wide scope, including electron-rich and electron-deficient benzenes, as well as naturally occurring heteroarenes. Electrophotochemical C?H trifluoromethylation was further achieved in flow with a modular electro-flow-cell equipped with an in-operando monitoring unit for on-line flow-NMR spectroscopy, providing support for the single electron transfer processes.

Design and implementation of a catalytic electron donor?acceptor complex platform for radical trifluoromethylation and alkylation

Electron donor?acceptor (EDA) complexes can controllably generate radicals under mild conditions through selective photoexcitation events. However, unproductive reactivity from fast deactivation of the photoexcited complexes through back electron transfer has slowed the development of EDA complexes in synthetic methodology. Here, we disclose the study of EDA complexes derived from 2-methoxynaphthalene donor and acylated ethyl isonicotinate N-oxide acceptor that undergo a fast N?O bond fragmentation event upon photoexcitation. This reaction design not only overcomes the limitations of back electron transfer but also enables regeneration of the donor species, representing a rare example of EDA photochemistry in a catalytic regime. The synthetic utility is demonstrated through visible light-driven radical trifluoromethylation and Minisci alkylation reactions. The scalability of the EDA complex-promoted reaction is evidenced by the successful multigram-scale trifluoromethylation of methyl N-Boc pyrrole-2-carboxylate in a continuous flow manifold.

Alternating current electrolysis for organic electrosynthesis: Trifluoromethylation of (hetero)arenes

Paired electrolysis has a limited reaction scope for organic synthesis because it is often not compatible with reactions involving short-lived intermediates. We addressed this limitation using alternating current electrolysis (ACE). Using trifluoromethyla

REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION

Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.

Energy-Efficient Solar Photochemistry with Luminescent Solar Concentrator Based Photomicroreactors

The sun is the most sustainable light source available on our planet, therefore the direct use of sunlight for photochemistry is extremely appealing. Demonstrated here, for the first time, is that a diverse set of photon-driven transformations can be efficiently powered by solar irradiation with the use of solvent-resistant and cheap luminescent solar concentrator based photomicroreactors. Blue, green, and red reactors can accommodate both homogeneous and multiphase reaction conditions, including photochemical oxidations, photocatalytic trifluoromethylation chemistry, and metallaphotoredox transformations, thus spanning applications over the entire visible-light spectrum. To further illustrate the efficacy of these novel solar reactors, medicinally relevant molecules, such as ascaridole and an intermediate of artemisinin, were prepared as well.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

M?C Bond Homolysis in Coinage-Metal [M(CF3)4]? Derivatives

A comparative study of the homoleptic [M(CF3)4]? complexes of all three coinage metals (M=Cu, Ag, Au) reveals that homolytic M?C bond cleavage is favoured in every case upon excitation in the gas phase (CID-MS2). Homolysis also occurs in solution by photochemical excitation. Transfer of the photogenerated CF3. radicals to both aryl and alkyl carbon atoms was also confirmed. The observed behaviour was rationalized by considering the electronic structure of the involved species, which all show ligand-field inversion. Moreover, the homolytic pathway constitutes experimental evidence for the marked covalent character of the M?C bond. The relative stability of these M?C bonds was evaluated by energy-resolved mass spectrometry (ERMS) and follows the order CuAg?Au. The qualitatively similar and rather uniform behaviour experimentally observed for all three coinage metals gives no ground to suggest variation in the metal oxidation state along the group.

Argentination of Fluoroform: Preparation of a Stable AgCF3 Solution with Diverse Reactivities

The transformation of a large-volume industrial by-product and stable greenhouse gas fluoroform (HCF3) to useful products has recently received significant attention. Now, a simple and scalable preparation of AgCF3 by treatment of HC

Ligand-free trifluoromethylation of iodoarenes by use of 2-Aryl-2-trifluoromethylbenzimidazoline as new trifluoromethylating reagent

N-Methyl 2-aryl-2-trifluoromethylbenzimidazolines were synthesized and utilized in the trifluoromethylation reaction of iodoarenes in the presence of copper(I) salt and base. Iodoarenes bearing electron-donating and electron-withdrawing groups were tolerant to this reaction in the absence of a ligand and gave trifluorotoluene derivatives in good to high yields.