135822-91-2

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 127-65-1 chloroamine-T 
• 100-55-0 3-hydroxymethylpyridin 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 174291-24-8 (1R,2R,3S,4S)-1,7,7-Trimethyl-3-methylsulfanyl-bicyclo[2.2.1]heptan-2-ol 
• 50530-37-5 2,5-Diphenyl-4-(3-pyridyl)imidazol 
• 1180611-49-7 dimethyl 5-methylene-2-(pyridin-3-yl)-1-tosylpyrrolidine-3,3-dicarboxylate 
• 5097-90-5 (Z)-3-styrylpyridine 
• 1361015-70-4 N-[2'-methylene-3'-oxo-1'-(pyridin-3''-yl)butyl]-4-methylbenzenesulfonamide 
• 1402429-47-3 ethyl 2,2-difluoro-3-(p-tolylsulfonylamino)-3-(3-pyridyl)propionate 
• 1421968-71-9 (2S,3S)-3-ethyl-4-methylene-2-(pyridin-3-yl)-1-tosylpyrrolidine-3-carbonitrile 

Relevant academic research and scientific papers

Rhodium-Catalysed Asymmetric Arylation of Pyridylimines

The catalytic asymmetric arylation of pyridylimines was developed. A range of pyridylimines reacted with arylboronic acids under rhodium catalysis to produce pyridine-incorporating chiral diarylmethylamines in 46% to 99% yield with 90:10 to 99.5:0.5 er, thus providing a method for the preparation of these important chiral pharmacophores. (Figure presented.).

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

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.

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.

A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines

The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.

Base and copper(i) catalyzed Mannich, alkyne hydroamination cascades for the direct synthesis of 2-methylenepyrrolidines

An efficient, simple-to-perform, one-pot reaction cascade to 2-methylenepyrrolidines from p-toluenesulfonyl protected imines and propargylated malonates under a combination of base and copper(i) catalysis is reported.

Copper-catalyzed N-alkylation of sulfonamides with benzylic alcohols: Catalysis and mechanistic studies

The N-alkylation of sulfonamides with alcohols is efficiently performed in the presence of easily available copper catalysts via hydrogen borrowing methodology. Applying a copper acetate/potassium carbonate system the reaction of sulfonamides and alcohols gave the corresponding secondary amines in excellent yield. In situ HR-MS analysis indicated that bissulfonylated amines are formed under air atmosphere, which act as self-stabilizing Iigands for the catalytic system. UV-visible measurements suggest the interaction between the copper centre and the bissulfonylated amine. Reactions of benzyl alcohol-d 7 with p-toluenesulfonamide, Nbenzyl-p-toluenesulfonamide or N-benzylidenetoluenesulfonamide revealed that the reaction proceeds via a transfer hydrogenation mechanism and the whole process is micro-reversible. Competitive reactions of benzyl alcohol and benzyl alconol-d7 with ptoluenesulfonamide revealed a kinetic isotope effect (kH/kD) of 3.287 (0.192) for the dehydrogenation of benzyl alcohol and 0.611 (0.033) for the hydrogenation of the N-benzylidene-p-toluenesulfonamide intermediate, which suggests that dehydrogenation of the alcohol is the rate-determining step.

A novel method for the synthesis of N-sulfonylaldimines by ZnO as a recyclable neutral catalyst under solvent-free conditions

ZnO acts as an effective catalyst for the rapid synthesis of a range of N-sulfonylaldimines from aromatic aldehydes and sulfonamides under solvent free conditions. The ZnO powder can be reused up to three times after simple washing with distilled water and ethyl acetate.