97305-99-2

Upstream product

• 947-91-1 Diphenylacetaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 530-48-3 1,1-Diphenylethylene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 645-49-8 cis-stilben 
• 94286-08-5 N-(p-toluenesulfonyl)-2,2-diphenylaziridine 
• 884866-01-7 1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 
• 98-80-6 phenylboronic acid 
• 97306-00-8 N-(2,2-Diphenyl-2-hydroxyethyl)toluene-p-sulphonamide 

Downstream Products

• 97306-02-0 N-benzyl-N-(2,2-diphenylethenyl)toluene-p-sulphonamide 
• 727416-65-1 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole 
• 65996-43-2 N₁-(1-methyl-2-oxo-2-phenylethyl)-4-methyl-1-benzenesulfonamide 
• 3316-42-5 N-(2-hydroxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

A practical synthesis of N-tosylimines of arylaldehydes

Synthesis of N-tosylimines of arylaldehydes was carried out by the reaction of arylaldehydes and p-toluenesulfonamide in methylene chloride in the presence of trifluoroacetic anhydride as a dehydrating agent.

Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight

Olefin aziridination via organocatalytic nitrene transfer offers potential complementarity to metal-catalyzed methods; however there is a lack of reports of such reactions in the literature. Herein is reported a method that employs an iminium salt to cata

A Novel Catalyst-Free Synthesis of 2,2-Diaryl Enamides from Stilbenes via a Nitrene Transfer Reaction

A novel catalyst-free nitrene transfer reaction between stilbenes and iminoiodinanes was achieved for the first time, which provides an efficient and environmentally friendly way to access variously substituted 2,2-diaryl enamides under mild conditions. Mechanistic investigations suggested the reaction proceed via nitrene transfer and aromatic rearrangement with iminoiodinane also acting as a Lewis acid, benefitting the ring-opening of the aziridine intermediate.

Iridium-Catalyzed Isomerization of N-Sulfonyl Aziridines to Allyl Amines

The Crabtree's reagent catalyzes the isomerization of N-sulfonyl 2,2-disubstituted aziridines to allyl amines. The selectivity of allyl amine vs imine is very high (up to 99/1). The unprecedented isomerization takes place in mild conditions without activation of the catalyst by hydrogen. The mechanism has been studied computationally by DFT calculations; instead of the usual hydrogenation of COD, the catalytic species is formed by a loss of the pyridine ligand. Approaching of aziridine to this unsaturated species leads to a carbocation intermediate through a low energy barrier. A metal-mediated tautomerization involving sequentially γ-H elimination and N-H reductive elimination affords selectively the allyl amine. The readiness of the CγH bond to participate in the H elimination step accounts for the selectivity toward the allyl amine product.

A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: Catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations

A CuI catalyst (1), supported by a framework of strongly basic guanidinato moieties, mediates nitrene-transfer from PhI=NR sources to a wide variety of aliphatic hydrocarbons (C-H amination or amidination in the presence of nitriles) and olefins (aziridination). Product profiles are consistent with a stepwise rather than concerted C-N bond formation. Mechanistic investigations with the aid of Hammett plots, kinetic isotope effects, labeled stereochemical probes, and radical traps and clocks allow us to conclude that carboradical intermediates play a major role and are generated by hydrogen-atom abstraction from substrate C-H bonds or initial nitrene-addition to one of the olefinic carbons. Subsequent processes include solvent-caged radical recombination to afford the major amination and aziridination products but also one-electron oxidation of diffusively free carboradicals to generate amidination products due to carbocation participation. Analyses of metal- and ligand-centered events by variable temperature electrospray mass spectrometry, cyclic voltammetry, and electron paramagnetic resonance spectroscopy, coupled with computational studies, indicate that an active, but still elusive, copper-nitrene (S = 1) intermediate initially abstracts a hydrogen atom from, or adds nitrene to, C-H and C=C bonds, respectively, followed by a spin flip and radical rebound to afford intra- and intermolecular C-N containing products.

Arylation of rhodium(II) azavinyl carbenes with boronic acids

A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.

N-Alkylation of some Secondary Styryl Enamides

The preparation of some secondary styryl enamides of both the Z-and E-configuration, and their exclusively N-alkylation through their anions is described.Partial configurational inversion is observed under certain conditions during the alkylation of the d