6462-34-6

Usage

InChI:InChI=1/C13H12O2S/c1-16(14,15)13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10H,1H3

Upstream product

• 92-52-4 biphenyl 
• 7143-01-3 Methanesulfonic anhydride 
• 3466-32-8 4-bromoohenyl methyl sulfone 
• 98-80-6 phenylboronic acid 
• 5122-94-1 4-biphenylboronic acid 
• 20277-69-4 sodium methansulfinate 
• 3144-09-0 methanesulfonamide 
• 1591-31-7 4-iodo-biphenyl 
• 67-68-5 dimethyl sulfoxide 
• 124-63-0 methanesulfonyl chloride 
• 98-57-7 4-chlorophenyl methyl sulfone 
• 110-05-4 di-tert-butyl peroxide 
• 616-38-6 carbonic acid dimethyl ester 
• 701-34-8 4-bromo-benzenesulfonic acid amide 

Relevant academic research and scientific papers

Pd–Ni bimetallic catalyst supported on dendrimer-functionalized magnetic graphene oxide for efficient catalytic Suzuki-Miyaura coupling reaction

A novel type of dendritic structure was grown on the magnetic graphene oxide nanocomposite surface through thiol-ene click reaction. The resulting nanocomposite was utilized as a support for immobilizing Pd–Ni bimetallic nanoparticles, which were employed

High Chemoselectivity in the Construction of Aryl Methyl Sulfones via an Unexpected C-S Bond Formation between Sulfonylhydrazides and Dimethyl Phosphite

A highly chemoselective route to aryl methyl sulfones via an unexpected C S bond formation between sulfonylhydrazides and dimethyl phosphite catalyzed by NaI under mild conditions has been established. This transformation provides an alternative and metal-free pathway to acquire various aryl methyl sulfones in good to excellent yields. Notably, dimethyl phosphite was employed as a stable and readily available alkyl source.

Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light

Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.

Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates

A magnetic nanocatalyst was purveyed as a heterogeneous recoverable palladium-based catalyst anchored on green, sustainable and phosphine free support. Resulted Fe3O4@SiO2-Phen-Pd(0) nanocatalyst bearing powerful phenanthroline ligand was thoroughly characterized by physicochemical approaches like UV–vis, FT-IR, EDX, XRD, TGA, ICP, VSM, DLS, FESEM, and TEM analyses. After finding trustable data, the obtained magnetic catalyst was considered to be applied in the Suzuki-Miyaura type C-C couplings and getting corresponding tetrazoles using arylboronic acid derivatives as alternate precursors of aromatic halides and stupendous data were observed.

Preparation method of methyl sulfone compound

The invention discloses a synthesis method of a methyl sulfone compound, which comprises the following steps: by using an iodinated compound as a substrate, adding a sulfite compound into the substrate, and using a 1, 4-dioxane solution as a solvent, heating under the protection of nitrogen under the actions of a silicon reagent, a phase transfer catalyst and a palladium catalyst to obtain a crudeproduct; then purifying the crude product, firstly filtering the crude product, and removing the solvent to obtain residues; carrying out silica gel column chromatography on the residues, leaching with eluent, and collecting effluent; combining the effluent containing the product; and concentrating the combined effluent to remove the solvent, and finally carrying out vacuum drying to obtain the target product. The method has the advantages of simple process flow, easiness in product purification, environmental safety and high yield.

General sulfone construction: Via sulfur dioxide surrogate control

A highly efficient one-step synthesis of alkyl-alkyl and aryl-alkyl sulfones with a facile combination of halides, sulfur dioxide surrogates and phosphate esters is described. When thiourea dioxide was employed as a reductive sulfur dioxide surrogate, alkyl-alkyl sulfones were obtained under transition metal free conditions. Aryl-alkyl sulfones were obtained with an extremely low catalytic loading (0.2 mol%) via altering the mask of sulfur dioxide surrogates to sodium dithionite. A phosphate ester was employed as a stable and readily available alkyl source. Notably, this protocol has been applied to the late-stage modification of natural products and bioactive molecules.

Immobilized Pd on a NHC functionalized metal–organic framework MIL-101(Cr): an efficient heterogeneous catalyst in Suzuki?Miyaura coupling reaction in water

A novel Pd?NHC functionalized metal–organic framework (MOF) based on MIL-101(Cr) was synthesized and used as an efficient heterogeneous catalyst in the C-C bond formation reactions. Using this heterogeneous Pd catalyst system, the Suzuki?Miyaura coupling reaction was accomplished well in water, and coupling products were obtained in good to excellent yields in short reaction time. The Pd?NHC?MIL-101(Cr) was characterized using some different techniques, including Fourier transform-infrared, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy (TEM), X-ray photoelectron spectroscopy, inductively coupled plasma and elemental analysis. The microscopic techniques showed the discrete octahedron structure of MIL-101(Cr), which is also stable after chemical modification process to prepare the catalyst system. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the structure of the catalyst, while no reducing agent was used. It seems that the NHC groups and imidazolium moieties in the structure of the MOF can reduce Pd (II) to Pd (0) species. This modified MOF substrate can also prevent aggregation of Pd nanoparticles, resulting in high stability of them in organic transformation. The Pd?NHC?MIL-101(Cr) catalyst system could be simply extracted from the reaction mixture, providing an efficient synthetic method for the synthesis of biaryls derivatives using the aforementioned coupling reaction. The Pd?NHC?MIL-101(Cr) catalyst could be recycled in this organic reaction with almost consistent catalytic efficiency.

Ni: Vs. Pd in Suzuki-Miyaura sp2-sp2 cross-coupling: A head-to-head study in a comparable precatalyst/ligand system

The Suzuki-Miyaura reaction is a cornerstone method for sp2-sp2 cross-coupling in industry. There has been a concerted effort to enable the use of Ni catalysis as an alternative to Pd in order to mitigate cost and improve sustainability. Despite significant advances, ligand development for Ni-catalyzed Suzuki-Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study we evaluate the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context.

Aryl Methyl Sulfone Construction from Eco-Friendly Inorganic Sulfur Dioxide and Methyl Reagents

A three-component cross-coupling protocol of boronic acid, sodium metabisulfite, and dimethyl carbonate was developed for the construction of significant functional methyl sulfones, in which introduction of sulfur dioxide at the last stage was successfully achieved in one step. Inorganic sodium metabisulfite was used as an eco-friendly sulfur dioxide source. Green dimethyl carbonate was employed as methyl reagent in this transformation. Diverse functional methyl sulfones were obtained from various readily available boronic acids. Notably, the last-stage modification of pharmaceuticals and the synthesis of Firocoxib were efficiently established through this strategy.

HETEROCYCLIC CARBOXYLIC ACID AMIDE LIGAND AND APPLICATIONS THEREOF IN COPPER CATALYZED COUPLING REACTION OF ARYL HALOGENO SUBSTITUTE

Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C—N, C—O, C—S and other bonds.