17692-84-1

Upstream product

• 66-99-9 β-naphthaldehyde 
• 672-78-6 methyl p-toluene sulfinate 
• 6873-55-8 p-tolylsulfinyl amide 
• 103-19-5 di(p-tolyl) disulfide 
• 959865-49-7 N-(naphthalen-2-ylmethylidene)-p-toluenesulfinamide 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 17693-49-1 N'-(p-Toluolsulfonyl)-N,N-diethyl-α-(naphthyl-2-methylen)-propionamidin 
• 1198790-81-6 4-methyl-N-(1-(naphthalen-2-yl)-3-oxo-3-phenylpropyl)benzenesulfonamide 
• 1213707-18-6 ethyl (4S,5R)-5-(naphthalen-2-yl)-2-thioxo-1-tosylimidazolidine-4-carboxylate 
• 1207097-66-2 N-((S)-((R)-4-isopropyl-5-oxo-2-phenyl-4,5-dihydrooxazol-4-yl)(naphthalen-2-yl)methyl)-4-methylbenzenesulfonamide 
• 1231260-49-3 (3R,4S)-3-ethyl-4-(naphthalen-2-yl)-3-phenyl-1-tosylazetidin-2-one 
• 1234619-97-6 3,3-dimethyl-2-(naphthalen-2-yl)-1-tosyl-2,3-dihydropyridin-4(1H)-one 
• 1245746-96-6 (4R,5S)-4-(methoxycarbonyl)-5-(2-naphthyl)-N-tosyl-2-imidazoline 

Relevant academic research and scientific papers

Copper-boryl mediated transfer hydrogenation of N-sulfonyl imines using methanol as the hydrogen donor

B2Pin2-assisted copper-catalyzed transfer hydrogenation of aromatic sulfonylimines has been achieved, delivering a variety of aryl/heteroaryl sulfonamides in good to excellent yields under mild reaction conditions and with methanol a

Nickel-catalyzed kumada cross-coupling reactions of benzylic sulfonamides

Herein, we report a Kumada cross-coupling reaction of benzylic sulfonamides. The scope of the transformation includes acyclic and cyclic sulfonamide precursors that cleanly produce highly substituted acyclic fragments. Preliminary data are consistent with a stereospecific mechanism that allows for a diastereoselective reaction.

Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids

We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism of the full catalytic cycle, which consists of the selectivity-determining ring opening of the azetidine, reaction with water, rate-determining transmetalation, and reductive elimination. Transition states of the selectivity-determining ring-opening step were systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction. (Figure presented.).

NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant

A nickel-catalyzed reductive coupling of alkynes and imines using readily available isopropanol as the reducing agent was developed. The use of a sterically bulky and electron-rich carbene ligand (AnIPr) significantly promotes the reaction, providing various multi-substituted allylic amines in 23-89% yield and the corresponding chiral ligand (AnIPr-3) can afford the products in 51-95% ee.

Alkenyl Exchange of Allylamines via Nickel(0)-Catalyzed C-C Bond Cleavage

A functional group exchange reaction between allylamines and alkenes via nickel-catalyzed C - C bond cleavage and formation was developed. This reaction provides a novel protocol, which does not require the use of unstable imine substrates, for the synthesis of allylamines, which are widely used in the production of fine chemicals, pharmaceuticals, and agrochemicals.

Branched Amine Synthesis via Aziridine or Azetidine Opening with Organotrifluoroborates by Cooperative Br?nsted/Lewis Acid Catalysis: An Acid-Dependent Divergent Mechanism

A practical catalytic method to synthesize β,β- and γ,γ-substituted amines by opening aziridines and azetidines, respectively, using alkenyl, alkynyl, or aryl/heteroaryl trifluoroborate salts is described. This reaction features simple open-flask reaction conditions, the use of transition-metal-free catalysis, complete regioselectivity, and high diastereoselectivity. Preliminary mechanistic studies suggest that carbocation formation is disfavored. Stereoretentive addition is favored with Br?nsted acid present, while stereoinversion is favored in its absence, indicating divergent mechanisms.

Verkade's Superbase as an Organocatalyst for the Strecker Reaction

Proazaphosphatranes -Verkade's superbases- proved to be efficient organocatalysts for the Strecker reaction between protected imines and trimethylsilyl cyanide (TMSCN). Excellent to quantitative yields were reached and, compared to other systems, only low

Visible-Light-Mediated Decarboxylative Benzylation of Imines with Arylacetic Acids

A straightforward method for the visible-light-mediated decarboxylative benzylation of imines is reported. The key feature of this method is the use of simple primary, secondary, and tertiary arylacetic acids as precursors of benzyl radicals, enabling the facile benzylation of a variety of imines under mild conditions. A variety of structurally diverse β-arylethylamines (37 examples) was accessed using this method.

Highly Enantioselective Ferrocenyl Palladacycle-Acetate Catalysed Arylation of Aldimines and Ketimines with Arylboroxines

Benzylic N-substituted stereocenters constitute a frequent structural motif in drugs. Their highly enantioselective generation is hence of technical importance. An attractive strategy is the arylation of imines with organoboron reagents. Chiral Rh complexes have reached a high level of productivity for this reaction type. In this article we describe that an electron rich PdIIcatalyst also performs well in the arylation of aldimines, comparable to the best Rh catalysts. The ferrocenyl palladacycle-acetate catalyst allows for a broad substrate scope and very high enantioselectivities. Commonly observed side reactions like aryl–aryl homocouplings and imine hydrolysis could be blocked. Mechanistic studies implicate that a) the acetate ligand is crucial for transmetallation, b) the active catalyst is most likely a palladacycle-OAc monomer, c) the rate limiting step is probably the product release. By added KOAc the arylation could also be applied to ketimines.

Palladium-Catalyzed Direct Intramolecular C-N Bond Formation: Access to Multisubstituted Dihydropyrroles

A palladium-catalyzed intramolecular amination of alkenes with retention of olefin functionalization was achieved under mild reaction conditions. In the presence of palladium catalyst, the tosyl-protected amine can directly couple with a double bond to provide versatile dihydropyrrole derivatives in moderate to excellent yields.