143206-01-3

Upstream product

• 105-07-7 4-cyanobenzaldehyde 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 6873-55-8 p-tolylsulfinyl amide 
• 4083-64-1 Tosyl isocyanate 
• 127-65-1 chloroamine-T 

Downstream Products

• 1552-58-5 (Z)-4-cyanostilbene 
• 1294493-81-4 3-(4-cyanophenyl)-2-methylene-4-nitrobutanenitrile 
• 1285700-13-1 C₁₉H₁₈N₂O₃S 
• 1278585-52-6 C₂₅H₂₀N₂O₃S 
• 1264885-64-4 C₂₁H₁₈N₂O₃S 
• 777889-68-6 ethyl 3-(4-methylphenylsulfonamido)-3-(4-cyanophenyl)propanoate 
• 1180611-27-1 dimethyl 2-(4-cyanophenyl)-5-methylene-1-tosylpyrrolidine-3,3-dicarboxylate 
• 1160052-45-8 methyl 2-[(diphenylmethylene)amino]-3-(p-cyanophenyl)-3-(p-toluenesulfonylamino)propanoate 
• 1174514-20-5 4-((1S,2S)-2-nitro-3-phenyl-1-(tosylamino)but-3-enyl)benzonitrile 

Relevant academic research and scientific papers

Accelerated Reactivity Mechanism and Interpretable Machine Learning Model of N-Sulfonylimines toward Fast Multicomponent Reactions

We introduce chemical reactivity flowcharts to help chemists interpret reaction outcomes using statistically robust machine learning models trained on a small number of reactions. We developed fast N-sulfonylimine multicomponent reactions for understanding reactivity and to generate training data. Accelerated reactivity mechanisms were investigated using density functional theory. Intuitive chemical features learned by the model accurately predicted heterogeneous reactivity of N-sulfonylimine with different carboxylic acids. Validation of the predictions shows that reaction outcome interpretation is useful for human chemists.

One-Pot Synthesis of Diazirines and 15N2-Diazirines from Ketones, Aldehydes and Derivatives: Development and Mechanistic Insight

Broad scope one-pot diazirine synthesis strategies have been developed using two different oxidants depending on the nature of the starting material. In all cases, an inexpensive commercial solution of ammonia (NH3) in methanol (MeOH) was emplo

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles

The MgI2 mediated reaction of aryl substituted cyclopropyl nitriles with tosyl aldimines to give 2,3-diaryl-3-cyano-substituted pyrrolidines has been demonstrated. In all cases, the trans-diastereoisomer was determined to be the major product.

Ruthenium-Catalyzed Synthesis of Isoindolinones via Amide-Directed Addition of Aromatic C-H Bonds to Aldimines

Ruthenium-catalyzed addition of aromatic C-H bonds to aldimines is described. [RuCl2(p-cymene)]2 functions as an efficient catalyst to promote the coupling of aryl amides with aldimines in the presence of a catalytic amount of base to give the corresponding isoindolinone derivatives. The nature of the substituent at the N-atom of the amides is crucial for the efficient conversion of the substrates, and a p-toluenesulfonyl group is the functionality of choice. A variety of amides and aldimines participated in the present Ru-catalyzed reaction to furnish the corresponding isoindolinones in moderate to high yield.

Visible-light, iodine-promoted formation of n-sulfonyl imines and n-alkylsulfonamides from aldehydes and hypervalent iodine reagents

Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes,

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.

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.

Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes

A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.