852292-23-0

Upstream product

• 110-86-1 pyridine 
• 599-86-0 4-methyl-N-(4-methylphenyl)benzenesulfonamide 
• 29289-13-2 2-iodo-4-methylaniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 106-49-0 p-toluidine 

Downstream Products

• 1242046-82-7 7-methyl-1-phenylquinoxalin-2(1H)-one 
• 1431882-06-2 2,6-dimethyl-5-tosyl-5,6-dihydroindolo[2,3-b]indole 
• 852292-32-1 N-[2-(3-hydroxy-prop-1-ynyl)-4-methyl-phenyl]-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

A new preparative route to substituted carbazoles by benzannulation

A new regioselective pathway to substituted carbazole derivatives is described here. According to this procedure substituted 2-alkoxycarbonyl-4- acetoxy-9-(p-toluenesulfonyl) carbazoles are obtained by treatment of substituted 6-[2-(p-toluenesulfonyl-amin

Palladium-Catalyzed Enantioselective Intramolecular Heck Carbonylation Reactions: Asymmetric Synthesis of 2-Oxindole Ynones and Carboxylic Acids

Herein, we report a Pd-catalyzed enantioselective domino Heck carbonylation reaction of o-iodoacrylanilides with terminal alkynes and water as the nucleophiles, affording a diversity of β-carbonylated 2-oxindole derivatives bearing a 3,3-disubstituted all-carbon quaternary stereocenter, in high yields (55–99 %) with good to excellent enantioselectivities (up to 99 % ee). The synthetic utilities of the protocol were demonstrated in the gram-scale synthesis of 2-oxindole-derived ynone 3 ea and carboxylic acid 4 a, as well as the facile synthesis of chiral 2-oxindoles with a pyrazole or isoxazole moiety.

Asymmetric Counteranion Directed Catalytic Heck/Tsuji-Trost Annulation of Aryl Iodides and 1,3-Dienes

A chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction of aryl iodides and 1,3-dienes is presented. Chiral indoline derivatives could be afforded with remarkably higher yields and enantioselectivities than our previous chiral ligand-based method. Silver carbonate is employed as both base and halide scavenger to ensure fast and recyclable exchange of the catalytic amount of chiral anions. Fast salt metathesis, as well as the acceleration effect of the chiral anion, could both benefit the stereocontrol of the reaction.

Palladium-Catalyzed Allenamide Carbopalladation/Allylation with Active Methine Compounds

A palladium-catalyzed allenamide carbopalladation/allylation with active methine compounds has been developed. Various indoles and isoquinolinones bearing a quaternary carbon center were achieved with good efficiency, a broad substrate scope and good functional group tolerance. This reaction underwent cascade oxidative addition, carbopalladation, and allylic alkylation, and two new C-C bonds were formed in one pot.

Nickel-Catalyzed trans-Carboamination across Internal Alkynes to Access Multifunctionalized Indoles

A Ni-catalyzed reaction was developed for the synthesis of multifunctionalized indoles. The reaction proceeded through oxidative cyclization of the Ni(0)/P^N complex with an enyne system, 2-alkynyl anilinoacrylate, to provide a nickelacycle intermediate. The trans-carboamination around the internal alkyne was achieved by syn/anti-rotation of the Ni-carbenoid intermediate formed by C-N bond cleavage of the nickelacycle, and 3-alkenylated indoles were formed by C-N bond-forming reductive elimination. Notably, the synthesized indoles could be successfully transformed to functionalized carbazoles.

Parallel strategies for the synthesis of annulated pyrido[3,4-b]indoles via Rh(I)- and Pd(0)-catalyzed cyclotrimerization

Two different pathways for the synthesis of annulated pyrido[3,4-b]indoles are reported using metal-catalyzed cyclotrimerization reactions. A stepwise process using Rh(I)-catalysis in the final step of the synthesis and a multicomponent, tandem catalytic

Synthesis and optical properties of 2-functionally substituted 4,5-dihydrothieno[3,2-c]quinolines

N-Protected 4-(anilinomethyl)thiophene-2-carbaldehydes were prepared by the reaction of easily available 4-chloromethylthiophene-2-carbaldehyde with N-(2-halogenophenyl) substituted acetamides, 4-methylbenzenesulfonamides and carbamates in the presence of K2CO3 or Cs2CO3. The compounds obtained were converted to 4,5-dihydrothieno [3,2-c]quinoline-2-carbaldehydes by palladium catalyzed intramolecular cyclization in homogenous or heterogenous (Pd/C) conditions with good yields and subsequently used for preparing of 2-functionally substituted thieno [3,2-c]quinoline derivatives (nitriles, carboxamides, carboxylic acids, esters). The optical properties of 2-functionally substituted thieno[3,2-c]quinolines and 4H-thieno[3,2-c]chromenes have been studied. Moderate to high fluorescence quantum yields are observed for these compounds ranging from 0.15 to 0.87. Structure - optical properties relationships have been established for the compounds synthesized, and their prospective application as invisible ink dyes was practically demonstrated.

Dehydrogenation of N-Heterocycles by Superoxide Ion Generated through Single-Electron Transfer

Nitrogen-containing heteroarene motifs are found in numerous pharmaceuticals, natural products, and synthetic materials. Although several elegant methods for synthesis of these compounds through dehydrogenation of the corresponding saturated heterocycles have been reported, some of the methods are hampered by long reaction times, harsh conditions, and the need for catalysts that are not readily available. This work reports a novel method for dehydrogenation of N-heterocycles. Specifically, O2.? generated in situ acts as the oxidant for N-heterocycle substrates that are susceptible to oxidation through a hydrogen atom transfer mechanism. This method provides a general, green route to N-heteroarenes.

Tris(trimethylsilyl)silane and visible-light irradiation: A new metal- and additive-free photochemical process for the synthesis of indoles and oxindoles

A combined tris(trimethylsilyl)silane and visible-light-promoted intramolecular reductive cyclization protocol for the synthesis of indoles and oxindoles has been developed. This straightforward and efficient method shows tolerance towards a broad spectru

Palladium-catalyzed intramolecular reductive cross-coupling of Csp 2-Csp3 bond formation

A Pd-catalyzed efficient reductive cross-coupling reaction without metallic reductant to construct a Csp2-Csp3 bond has been reported. A PdIV complex was proposed to be a key intermediate, which subsequently went through d