72496-80-1

Upstream product

• 120-72-9 indole 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 1849-36-1 para-nitrobenzenethiol 
• 2937-05-5 4-nitrobenzenesulfonohydrazide 
• 100-00-5 4-chlorobenzonitrile 
• 13165-85-0 ethyl p-nitrobenzenesulphinate 
• 636-98-6 p-nitrobenzene iodide 
• 51221-38-6 N-hydroxy-4-nitrobenzenesulfonamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 17796-89-3 1-[(4-nitrophenyl)sulfanyl]pyrrolidine-2,5-dione 
• 1199-67-3 4-nitro-benzenesulfinic acid 
• 937-32-6 4-nitrobenzenesulfenyl chloride 

Relevant academic research and scientific papers

A rapid synthesis of 3-sulfenyl indoles using Selectfluor

The direct 3-arylthiolation of indoles with aromatic thiols has been achieved in the presence of Selectfluor under mild conditions to produce 3-arylthioindoles in relatively good to excellent yields and with high selectivity. This method is effective even

Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation

A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barr

Palladium-Catalyzed Direct C2-Biarylation of Indoles

Biaryl and indole units are important structural motifs in several bioactive molecules and functional materials. We have accomplished straightforward access to C2-biarylated indole derivatives through palladium-catalyzed C-H activation strategy with a bro

TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME

An efficient TBAI (tetrabutylammonium iodide)-mediated C–H sulfenylation of arenes with arylsulfonyl hydrazides in dipropylene glycol dimethyl ether (DPDME) was described. Various electron-rich arenes were applicable in the reaction, such as naphthylamine, naphthol, aniline, indole, pyrrole, and imidaz o [1,2-a] pyridine. A wide range of the aryl sulfides were obtained with good functional group tolerance. This method features green reaction conditions (odorless and easily available sulfur reagent, recyclable TBAI, and DPDME as solvent), and broad substrate scope. The synthetic potential is demonstrated by gram-scale synthesis and downstream transformations. The mechanism studies show that the reaction is achieved through electrophilic substitution process, and diaryl disulfide may be the main intermediate.

Cuprous complex, preparation method thereof and application of cuprous complex in synthesis of 3-indolyl thioether

The invention relates to a cuprous complex, a preparation method thereof and an application of the cuprous complex in synthesis of 3-indolyl thioether. The structural formula of the cuprous complex isshown in the specification, Ar is aryl containing a benzene ring or heterocyclic aryl, and ''.'' is a boron hydrogen bond; the preparation method comprises the following steps: 1) dissolving ortho-carborane diformaldehyde and arylamine in an organic solvent, reacting at 60-100 DEG C, and cooling to room temperature after the reaction is finished; and 2) adding CuI, reacting at room temperature for 3-6 hours, and separating to obtain the cuprous complex. Compared with the prior art, the cuprous complex containing the ortho-position carborane Schiff base ligand can efficiently catalyze the coupling reaction of synthesizing a 3-indolyl thioether compound from indole and thiophenol, the method has the advantages of high selectivity, low catalyst dosage, mild reaction conditions, open reaction(taking air as an oxidant), high reaction rate, high yield, wide substrate range and the like and shows a wide industrial application prospect.

NH4I/1,10-phenanthroline catalyzed direct sulfenylation of N-heteroarenes with ethyl arylsulfinates

An efficient synthesis of N-heterocyclic aryl sulfides via NH4I/1,10-phenanthroline-catalyzed direct sulfenylation reactions was reported. In this reaction, heteroarenes such as indoles, and pyrroles serve as nucleophiles by installing a arylthio group at the C3 and C2 position of heterocycles, respectively. With readily accessible and free of unpleasant odor ethyl arylsulfinates as sulfur reagents, the metal-free-catalyzed direct sulfenylation of N-heteroarenes has been developed. 3-Arylthio-indoles and 2-arylthio-pyrroles derivatives were obtained in moderate to excellent yields, even on gram scale. The reaction was general for a broad scope of substrates and demonstrated good tolerance to a variety of functional groups.

Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot

Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.

Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Crystal structure, DFT study and catalytic investigation of palladium and nickel complexes towards deacylative sulfenylation of active methylenes and regioselective 3-sulfenylation of indoles: Via thiouronium salt formation

A series of Ni(ii), Cu(ii), Co(ii), and Pd(ii) complexes have been synthesized with a chelating Schiff base ligand coordinated to a metal center with ONS donor atoms. The ligand and complexes are characterized by elemental analysis and spectroscopic techniques like FT-IR, 1H-NMR, and UV-Visible spectroscopy. The single crystal structure of the Pd(ii) complex is obtained by X-ray diffraction analysis and exhibits slightly distorted square planar geometry. The structure is optimized by DFT, TD-DFT calculation to elaborate the electronic structure and NBO for the charge distribution analysis of the Pd(ii) complex. The synthesized Pd(ii) and Ni(ii) complexes as catalysts have been investigated in the C-S cross-coupling of indoles and active methylenes. The metal propelled regioselective transformation afforded 3-sulfenylated indoles while β-diketones favored deacylated monosulfenyl ketones in an excellent yield via thiouronium salt formation. The Pd(ii) complex displays slightly better reactivity whereas the Ni(ii) complex is cost-efficient. The method is fast, easy to handle and cost effective in terms of high reactivity of catalysts, use of non-toxic solvents, and cheaper aryl halides and thiourea replace conventional sulfur sources, providing a practical access to organic transformations.

Synthesis of 3-sulfenylindoles by Pd (II) nanoclusters confined within metal-organic framework fibers in aqueous solution

We have found that fibrous nanosilica (KCC-1) can used as a excellent support for the synthesis of highly sparse nanoparticles. KCC-1 has high surface area that was functionalized with 1,3-bis(dimethylthiocarbamoyloxy)benzene groups acting as the strong performers so that the Pd (II) was complex without aggregation on the fibers of the KCC-1 microspheres (KCC-1/BTB/Pd). For synthesis of 3-sulfenylindoles from aryl iodide, indoles, and thiourea used from the KCC-1/BTB/Pd NPs as a catalyst that showed excellent catalytic activities under green conditions. Compared with the traditional substrate, KCC-1/BTB/Pd substantially increases protection and the accessibility of the nanoparticle sites due to its three dimensional hierarchical structure.

Regioselective thiolation of electron rich arenes and heterocycles in recyclable catalytic media

A convenient and novel approach has been developed for the synthesis of unsymmetrical diaryl sulfides by the reaction of sulfonyl hydrazides with phenols using a [Bmim][Br] ionic liquid through the formation of C-S bonds. The reaction has further been extended to indole, β-naphthol and aromatic amine moieties. This protocol offers a new, versatile and greener approach for thiolation of natural phenols (monoterpenes)/aromatic phenols/β-naphthols/aromatic amines and indoles without using any catalyst. A broad range of functional groups were well tolerated in this reaction system.