13707-47-6

Upstream product

• 98-01-1 furfural 
• 622-58-2 p-Tolylisocyanate 
• 70-55-3 toluene-4-sulfonamide 
• 104-15-4 toluene-4-sulfonic acid 

Downstream Products

• 488720-06-5 N-(1,1-difuran-2-ylmethyl)-4-methylbenzenesulfonamide 
• 637019-53-5 (2R,5S,7S,1'RS)-7-(N-tosylamino-furan-2-yl-methyl)-8-oxo-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octane 
• 909296-49-7 (R_S,S)-N-[3-(furan-2-yl)-3-(N-tosylamino)-1-phenyl-propylidene]-tert-butanesulfinamide 
• 121564-33-8 N-tosylfurfurylamine 
• 134340-62-8 N-(1-furan-2-yl-ethyl)-4-methyl-benzenesulfonamide 
• 134340-63-9 (+/-)-4-methyl-N-(1-furan-2-ylpropyl)benzenesulfonamide 
• 134340-66-2 N-tosyl-α'-isobutyl-α-furfuryl amine 
• 595577-65-4 N-(1-furan-2-yl-2-methyl-propyl)-4-methyl-benzenesulfonamide 
• 134340-65-1 N-(1-(furan-2-yl)pentyl)-4-methylbenzenesulfonamide 
• 134340-64-0 N-tosyl-α'-propyl-α-furfuryl amine 

Relevant academic research and scientific papers

Desymmetrisation of meso difuryl alcohols, diols and their derivatives: Complementary directed and undirected asymmetric dihydroxylation reactions

Asymmetric reactions (for example, asymmetric epoxidation and asymmetric dihydroxylation) were examined for the desymmetrisation of the meso substrates 1,1-difuran-2-ylmethanol,N-(1,1-difuran-2-ylmethyl)-4- methylbenzenesulfonamide, (R,S)-1,4-difuran-2-yl

Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

Chiral-Directing-Group-Assisted Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C?H Bond to Aldimines with Subsequent Intramolecular Cyclization

By using a chiral directing group, an asymmetric rhodium(III)-catalyzed C?H bond addition to aldimines followed by intramolecular cyclization to form chiral isoindolinones has been achieved (up to 68 % yield, up to 93 % ee). A three-component variant that resembles Mannich reaction was also realized (41 % yield, 83 % ee). Product elaborations and preliminary mechanistic studies were described.

Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones

The synthesis of 3-alkyliden-2,3-dihydro-4-quinolones has been accomplished in a domino fashion through a three-step sequence that comprised an initial aza-Baylis-Hillman reaction, followed by a 1,3-rearrangement and an intramolecular amination. Starting from readily available aryl vinyl ketones and N-tosyl imines, the reaction with PPh3, CsOAc and CuI in CH3CN gave rise, in good overall yields, to final 3-alkyliden-4-quinolone derivatives, valuable scaffolds in medicinal chemistry. The simultaneous addition of two bases, PPh3 and CsOAc, was found to be crucial for the success of the process. While PPh3 promoted the reversible aza-Baylis-Hillman reaction, CsOAc triggered the subsequent 1,3-rearrangement, which shifted the initial equilibrium and allowed to complete the synthetic sequence upon the addition of CuI. (Figure presented.).

Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.

Iridium-Catalyzed Highly Regioselective and Diastereoselective Allylic Etherification to Access cis-2,6-Disubstituted Dihydropyridinones

A highly regio- and diastereoselective method to access cis-2,6-disubstituted dihydropyridinones under mild conditions by an iridium-catalyzed allylic etherification is reported. cis-2,6-Disubstituted dihydropyridinones are important precursors for the de novo synthesis of the corresponding piperidine alkaloids and iminosugars. This strategy features a broad substrate scope, high yields, and excellent regio- and diastereoselectivities. A π-allyl-Ir intermediate is involved in the mechanism. The strong A1,3-strain from the tosyl group may also favor the formation of cis-products in this transformation.

Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines

A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.

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

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.

Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles

Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.