940289-80-5

Upstream product

• 108-86-1 bromobenzene 
• 3796-24-5 4-trifluoromethylpyridine 
• 100-58-3 phenylmagnesium bromide 
• 2996-92-1 phenyl trimethylsiloxane 
• 118078-66-3 2-fluoro-4-(trifluoromethyl) Pyridine 
• 1008-89-5 2-phenylpyridine 
• 887144-94-7 Togni's reagent II 
• 1131-33-5 2-phenylpyridin N-oxide 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 175205-81-9 2-bromo-4-(trifluoromethyl)pyridine 
• 98-80-6 phenylboronic acid 
• 136964-14-2 (Z)-1-phenyl-4,4,4-trifluoro-2-buten-1-one 
• 3108-34-7 (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one 
• 100-52-7 benzaldehyde 

Downstream Products

• 1446325-87-6 C₂₀H₁₁F₃N₂O₂ 

Relevant academic research and scientific papers

Nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent

The first nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent has been achieved. Trifluoromethylation proceeds smoothly under mild conditions with moderate functional group compatibility. Notable advantages of this method include the using of low cost of nickel catalyst, and its simple convenient operation.

Experimental and Computational Studies towards Chemoselective C?F over C?Cl Functionalisation: Reversible Oxidative Addition is the Key

Catalytic cross-coupling is a valuable tool for forming new carbon-carbon and carbon-heteroatom bonds, allowing access to a variety of structurally diverse compounds. However, for this methodology to reach its full potential, precise control over all competing cross-coupling sites in poly-functionalised building blocks is required. Carbon-fluorine bonds are one of the most stable bonds in organic chemistry, with oxidative addition at C?F being much more difficult than at other C-halide bonds. As such, the development of methods to chemoselectively functionalise the C?F position in poly-halogenated arenes would be very challenging if selectivity was to be induced at the oxidative addition step. However, metal-halide complexes exhibit different trends in reactivity to the parent haloarenes, with metal-fluoride complexes known to be very reactive towards transmetalation. In this current work we sought to exploit the divergent reactivity of Ni?Cl and Ni?F intermediates to develop a chemoselective C?F functionalisation protocol, where selectivity is controlled by the transmetalation step. Our experimental studies highlight that such an approach is feasible, with a number of nickel catalysts shown to facilitate Hiyama cross-coupling of 1-fluoronapthalene under base free conditions, while no cross-coupling with 1-chloronapthalene occurred. Computational and experimental studies revealed the importance of reversible C?Cl oxidative addition for the development of selective C?F functionalisation, with ligand effects on the potential for reversibility also presented.

Transition-Metal-Free Desulfinative Cross-Coupling of Heteroaryl Sulfinates with Grignard Reagents

A mild cross-coupling reaction of heteroaryl sulfinates with Grignard reagents has been developed under transition-metal-free conditions. This study provides an example of the SO22- as a leaving group in an aromatic system and an effective methodology for the construction of C-C bond.

N-heterocyclic carbene enabled rhodium-catalyzed ortho C(sp2)-H borylation at room temperature

We report a rhodium-catalyzed ortho C(sp2)-H borylation of 2-phenylpyridines using commercially available N-heterocyclic carbenes (NHCs) as ligand and pinacolatodiboron (B2pin2) as borylating reagent. The reaction could take place at room temperature, tolerating a wide range of functionalities and affording ortho borylated products in moderate to excellent yields. The current method is also applicable to gram-scale reaction with reduced catalyst loading.

Structure- and Ligand-Based Discovery of Chromane Arylsulfonamide Nav1.7 Inhibitors for the Treatment of Chronic Pain

Using structure- and ligand-based design principles, a novel series of piperidyl chromane arylsulfonamide Nav1.7 inhibitors was discovered. Early optimization focused on improvement of potency through refinement of the low energy ligand conformation and mitigation of high in vivo clearance. An in vitro hepatotoxicity hazard was identified and resolved through optimization of lipophilicity and lipophilic ligand efficiency to arrive at GNE-616 (24), a highly potent, metabolically stable, subtype selective inhibitor of Nav1.7. Compound 24 showed a robust PK/PD response in a Nav1.7-dependent mouse model, and site-directed mutagenesis was used to identify residues critical for the isoform selectivity profile of 24.

Visible Light Induced Rhodium(I)-Catalyzed C?H Borylation

An efficient visible light induced rhodium(I)-catalyzed regioselective borylation of aromatic C?H bonds is reported. The photocatalytic system is based on a single NHC?RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC-carboxylate ligand was critical to ensure the stability of the RhI complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C?H bond addition upon irradiation with blue LEDs, leading to a cyclometalated RhIII-hydride intermediate.

Synthesis method and application of terephthalyl alcohol-derived bidentate phosphite ligand

The invention discloses a synthesis method and an application of a terephthalyl alcohol-derived bidentate phosphite ligand. The ligand has the following structural formula defined in the specification, wherein R is H or t-Bu. The ligand is a white solid, and is stable in structure, simple in synthesis, high in yield and easy to prepare in large quantities; in a nitrogen atmosphere, the ligand anda palladium salt are subjected to reaction in an organic solvent to obtain a ligand/palladium catalyst, a Suzuki-Miyaura reaction is catalyzed, the reaction conversion rate is high and the substrate universality is high.

Directed: Ortho C-H borylation catalyzed using Cp?Rh(iii)-NHC complexes

Cp?Rh(NHC) complexes with bulky chiral bidentate NHC-carboxylate ligands were efficiently synthesized and fully characterized including solid-state structures. These unprecedented rhodium(iii) complexes demonstrated high selectivity in pyridine-directed ortho-C-H borylation of arenes under mild conditions.

Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides

An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.

α-Halo carbonyls enable: Meta selective primary, secondary and tertiary C-H alkylations by ruthenium catalysis

A catalytic meta selective C-H alkylation of arenes is described using a wide range of α-halo carbonyls as coupling partners. Previously unreported primary alkylations with high meta selectivity have been enabled by this methodology whereas using straight chain alkyl halides affords ortho substituted products. Mechanistic analysis reveals an activation pathway whereby cyclometalation with a ruthenium(ii) complex activates the substrate molecule and is responsible for the meta selectivity observed. A distinct second activation of the coupling partner allows site selective reaction between both components.