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Upstream product

• 104-94-9 4-methoxy-aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 1150-26-1 N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide 
• 106-96-7 propargyl bromide 

Downstream Products

• 34129-41-4 N-p-toluenesulfonyl-6-methoxy-1,2-dihydroquinoline 
• 1395894-78-6 C₂₅H₂₃NO₄S 
• 1395894-77-5 C₂₄H₂₃NO₄S 
• 1395894-85-5 C₁₇H₁₅NO₂ 
• 1395894-86-6 C₁₈H₁₅NO₂ 
• 1395894-91-3 6-methoxy-4-(4-methoxyphenyl)-1-tosyl-1,2-dihydroquinoline 

Relevant academic research and scientific papers

Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups

A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.

Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.

Dynamic Kinetic Resolution in Gold-Catalyzed (4 + 2)-Annulations between Alkynyl Benzaldehydes and Allenamides to Yield Enantioenriched All-Carbon Diarylalkylmethane Derivatives

This work reports the synthesis of diarylmethane derivatives via gold-catalyzed (4 + 2)-annulations between alkynyl benzaldehydes and allenamides, followed by an aza-Claisen rearrangement. Deuterium labeling and crossover experiments have been performed to confirm this proposed mechanism. With racemic 3-substituted allenamides in a substrate ratio (1:1), we employ chiral gold catalysts to achieve a dynamic kinetic resolution to obtain enantioenriched diarylalkylmethane derivatives with high e.r. levels (up to 93:7).

Straightforward synthesis, spectroscopic characterizations and comprehensive DFT calculations of novel 1-ester 4-sulfonamide-1,2,3-triazole scaffolds

For the first time, an efficient click azide?alkyne [3 + 2] cycloaddition reaction for synthesis of new 1-ester 4-sulfonamide-1,2,3-triazole derivatives was developed via a three-component reaction of N-propargylsulfonamides, sodium azide, and α-haloesters in a one pot method. The mild reaction conditions, avoiding the isolation of hazardous organic azides, good yields (65–78%), and commercially available and inexpensive starting materials are advantages of this cycloaddition reaction for synthesis of fine chemicals. The all desired products were characterized by FT-IR, 1H and 13C NMR spectroscopy. The HOMO-LUMO analysis (electrophilicity index), vibrational frequencies (FT-IR), 1H and 13C chemical shift values and Li+ and Na+ ion affinities of a desired product have been also calculated by density functional theory (DFT). Lithium ion affinity of the product was determined as 80.78 kJ/mol higher than its sodium ion affinity. The NICS index was used to confirm of the cation π interaction in complex of the synthesized product with Li+ and Na+ ions.

Iron-Mediated Cyclization of 1,3-Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene-Fused Chromenes

The synthesis of selenophene-fused chromene derivatives starting from 1,3-diynyl propargyl aryl ethers is reported herein. The method is based on carbon-carbon, carbon-selenium, selenium-carbon and carbon-selenium bonds formation in a one-pot protocol, using iron(III) chloride and dibutyl diselenide as promoters. The same reaction conditions were applied to propargyl anilines leading to the formation of 1-(butylselanyl)-selenophene quinolines. The results showed that the dilution and temperature of substrate addition had a crucial influence in the products obtained. When the substrates were added at room temperature, in the absence of a solvent, a mixture of products was obtained, whereas the slowly addition (15 min) of starting materials, as a dichloromethane solution, at 0 °C led to the product formation in good yields. The mechanistic study indicates that the cooperative action between iron(III) chloride and dibutyl diselenide was essential to promote the cyclization, whereas separately none of them was effective in promoting the cyclization. We proved the synthetic utility of heterocycles obtained in the Suzuki cross coupling reaction, giving the corresponding cross-coupled products in good yields. In addition, the organoselenium moiety was removed from the structures of products by using n-butyllithium. (Figure presented.).

Efficient synthesis, spectroscopic characterization and DFT based studies of novel 1-amide 4-sulfonamide-1,2,3-triazole derivatives

In the present study, for the first time 1-amide 4-sulfonamide-1,2,3-triazole scaffolds were synthesized by using an azide-alkyne Huisgen cycloaddition reaction. The target products were obtained in moderate to good yields (45–75%) by using catalytic CuI and green system H2O/EtOH. The easy availability of the inexpensive starting materials, avoiding isolation and handling of hazardous organic azides and mild reaction conditions make this method a valuable tool for generating functionalized 1,2,3-triazole derivatives. The unambiguous characterization of synthesized compounds was accomplished by using various spectroscopic techniques such as 1H NMR, 13C NMR, and FT-IR. The information regarding optimized geometry, were obtained by applying DFT/B3LYP-6-31G(d) method. The electrophilicity index, 1H and 13C chemical shift values, lithium and sodium ion affinities of the desired product 3b have been also calculated by the mentioned method. As a whole, the calculated results were found in close agreement to that of experimental data. The studies revealed that the compound 3b possesses good Li+ and Na+ affinity and cation π interaction plays a vital role in the complexation of 3b. For the first time, nucleus–independent chemical shift index was used to confirm the cation π interaction of 3b.

Gold-Catalyzed 1,2-Oxyalkynylation of N-Allenamides with Ethylnylbenziodoxolones

A gold-catalyzed 1,2-oxyalkynylation of N-allenamides with ethylnylbenziodoxolones (EBXs) has been achieved for the first time. The reaction, which follows a redox-neutral Au(I)/Au(III) catalytic pathway, was enabled in an attempt to exhaust the EBX reagents atom-economically by putting the nucleophilic carboxylate part of EBXs to appropriate use. This constitutes the first example for gold-catalyzed β-alkynylation of N-allenamides to construct highly valuable 1,3-enynes. The potential of the sequence is further documented by some follow-up transformations.

Transition-Metal-Free Stereoselective Borylation of Allenamides

Complete stereocontrol on the transition-metal-free hydroboration of the distal double bond of allenamides could be achieved when allenamides contained acetyl substituents, which provided exclusively the Z-isomer. The consecutive Pd-catalyzed cross-coupli

[3+2]-Annulation of platinum-bound azomethine ylides with distal C=C bonds of N-allenamides

A Pt-catalyzed, highly regioselective reaction between N-allenamides and imino-alkynes leading to pyrrolo[1,2-a]indoles is described. This represents the first example of [3+2]-annulation of Pt-bound azomethine ylides with the distal C=C bond of N-allenam

Enantioselective Oxidative (4+3) Cycloadditions between Allenamides and Furans through Bifunctional Hydrogen-Bonding/Ion-Pairing Interactions

BINOL-based N-trifluoromethanesulfonyl phosphoramides catalyze the enantioselective (4+3) cycloaddition between furans and oxyallyl cations, the latter being generated in situ by oxidation of allenamides. The chiral organic phosphoramide counteranion is proposed to engage in the activation of the oxyallyl cation intermediate through cooperative hydrogen-bonding and ion-pairing interactions, enabling an efficient chirality transfer that provide the final adducts with high diastereo- and enantioselectivities. Remarkably, the reaction shows a wide substrate scope that includes a variety of substituted allenamides and furans.