65017-76-7

Upstream product

• 372-48-5 2-fluoropyridine 
• 116332-61-7 N-methoxy-N-methyl-4-trifluoromethylbenzamide 
• 14040-11-0 tungsten hexacarbonyl 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 455-13-0 4-Iodobenzotrifluoride 
• 13939-06-5 molybdenum hexacarbonyl 
• 1370441-14-7 2,2,2-trichloro-1-(4-(trifluoromethyl)phenyl)ethanone 
• 74-89-5 methylamine 
• 67-56-1 methanol 
• 1891-90-3 p-trifluoromethylbenzamide 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 593-51-1 methylamine hydrochloride 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1427042-18-9 C₂₃H₂₁NO₂ 
• 1427042-12-3 (E)-2-(1,2-diphenylvinyl)-N-methyl-4-(trifluoromethyl)benzamide 
• 339094-67-6 N-cyclohexyl-4-(trifluoromethyl)benzamide 
• 411209-38-6 (piperidin-1-yl)-(4-(trifluoromethyl)phenyl)methanone 
• 447455-27-8 morpholino(4-(trifluoromethyl)phenyl)methanone 
• 447431-60-9 (pyrrolidin-1-yl)(4-(trifluoromethyl)phenyl)methanone 
• 728-86-9 phenyl[4-(trifluoromethyl)phenyl]methanone 

Relevant academic research and scientific papers

The Pd-catalyzed synthesis of difluoroethyl and difluorovinyl compounds with a chlorodifluoroethyl iodonium salt (CDFI)

Herein, we report a simple and efficient method for the direct installation of chlorodifluoroethyl group onto aromatic molecules of various aromatic amides with a new 2-chloro,2,2-difluoroethyl(mesityl)iodonium salt (CDFI). Moreover, the chlorodifluoroeth

Iridium-catalyzed, ligand-controlled directed alkynylation and alkenylation of arenes with terminal alkynes

We report iridium-catalyzed C-C formation between benzamides and terminal alkynes. With the choice of a suitable ligand, a C-H alkynylation or alkenylation product could be obtained selectively. The directed C-H alkynylation proceeded without the need for an external oxidant, while the directed C-H alkenylation likely involves an unusual vinylidene mechanism. This divergent reactivity provides access to both alkynylation and alkenylation products from the same set of starting materials.

Dealkoxylation ofN-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis

Lewis acid-assisted palladium-catalysed dealkoxylation ofN-alkoxyamides has been developed. This reaction proceeded smoothly with a range ofN-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.

Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines

Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N -methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.

Tandem Transformation of Aldoximes to N-Methylated Amides Using Methanol

Tandem conversion of aldoximes to N-methylated amides with methanol in presence of a single Ru(II) catalyst is accomplished through the Ru(II)-mediated rearrangement followed by the reductive N-methylation. Employing this protocol, several aldoximes were directly transformed to the N-methylated amides using methanol. Kinetic experiments with H218O advocated that the aldoxime is acted as the nucleophile during the aldoxime to amide rearrangement process. Involvement of nitrile intermediate during this transformation is realized from the kinetic study. (Figure presented.).

Ruthenium-Catalyzed Synthesis of N-Methylated Amides using Methanol

An efficient synthesis of N-methylated amides using methanol in the presence of a ruthenium(II) catalyst is realized. Notably, applying this process, tandem C-methylation and N-methylation were achieved to synthesize α-methyl N-methylated amides. In addition, several kinetic studies and control experiments with the plausible intermediates were performed to understand this novel protocol. Furthermore, detailed computational studies were carried out to understand the mechanism of this transformation.

Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions

Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.

Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides

Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.

Rhenium-Catalyzed Phthalide Synthesis from Benzamides and Aldehydes via C-H Bond Activation

The [4 + 1] annulation of benzamides and aldehydes for phthalide synthesis was achieved via rhenium-catalyzed C-H activation, which demonstrates an unprecedented reaction pattern distinct from those of other transition-metal catalyses. The reaction also features readily available starting materials, a wide scope for both electro-rich and electro-deficient substrates, and the elimination of homoannulation byproducts.

Super electron donors derived from diboron

Single-electron transfer is an important process in organic chemistry, in which a single-electron reductant (electron donor) acts as a key component. Compared with metal-based electron donors, organic electron donors have some unique advantages, such as tunable reduction ability and mild reaction conditions. The development of novel organic electron donors with good reduction ability together with ease of preparation is in high demand. Based on the pyridine-catalyzed radical borylation reaction developed in our laboratory, we have discovered that, the reaction system consisting of a diboron(4) compound, methoxide and a pyridine derivative could smoothly produce super electron donors in situ. Two boryl-pyridine based species, the major one being a trans-2H,2′H-[2,2′-bipyridine]-1,1′-diide borate complex and the minor one being a pyridine radical anion-borate complex, were observed and carefully characterized. These complexes were found to be organic super electron donors unprecedented in literature, and their formation mechanisms were studied by DFT calculations. The diboron/methoxide/pyridine system enables the preparation of organic super electron donors from easily accessible starting materials under mild conditions, which has the potential to be a general and practical single-electron reducing agent in organic synthesis.