19738-01-3

Upstream product

• 933-00-6 p-methylbenzenesulfenyl chloride 
• 536-74-3 phenylacetylene 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 657-84-1 sodium tosylate 
• 100-42-5 styrene 
• 98-59-9 p-toluenesulfonyl chloride 
• 618-34-8 1-chlorostyrene 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 98-81-7 1-bromovinylbenzene 
• 28995-88-2 1-methyl-4-((phenylethynyl)sulfonyl)benzene 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 19719-87-0 1-methyl-4-(phenethylsulfonyl)benzene 
• 92357-55-6 1-Methyl-4-((E)-2-phenyl-2-propylsulfanyl-ethenesulfonyl)-benzene 
• 92357-57-8 1-Methyl-4-((E)-2-phenyl-2-phenylsulfanyl-ethenesulfonyl)-benzene 
• 19721-97-2 C₂₂H₂₀O₂S₂ 
• 92357-58-9 C₂₁H₁₇ClO₂S₂ 
• 16212-08-1 (Z)-1-methyl-4-(styrylsulfonyl)benzene 
• 92357-73-8 C₂₁H₁₇ClO₄S₂ 
• 19721-96-1 (E)-4,4'-(1-phenylethene-1,2-diyldisulfonyl)bis(methylbenzene) 
• 92357-71-6 1-Methyl-4-((E)-2-phenyl-2-phenylmethanesulfonyl-ethenesulfonyl)-benzene 
• 92357-72-7 1-((E)-2-Benzenesulfonyl-2-phenyl-ethenesulfonyl)-4-methyl-benzene 
• 92357-70-5 1-Methyl-4-[(E)-2-phenyl-2-(propane-1-sulfonyl)-ethenesulfonyl]-benzene 
• 92357-69-2 1-((E)-2-Ethanesulfonyl-2-phenyl-ethenesulfonyl)-4-methyl-benzene 
• 92357-54-5 1-((E)-2-Ethylsulfanyl-2-phenyl-ethenesulfonyl)-4-methyl-benzene 
• 92357-56-7 1-((E)-2-Benzylsulfanyl-2-phenyl-ethenesulfonyl)-4-methyl-benzene 

Relevant academic research and scientific papers

Heteroleptic Copper-Based Complexes for Energy-Transfer Processes: E → Z Isomerization and Tandem Photocatalytic Sequences

Energy-transfer processes involving copper complexes are rare. Using an optimized heteroleptic copper complex, Cu(bphen)(XantPhos)BF4, photosensitized E → Z isomerization of olefins is demonstrated. The XantPhos ligand afforded sensitizers with improved catalyst stability, while the bphen ligand lengthened the excited-state lifetime. A series of 25 di- and trisubstituted alkenes underwent photoisomerization, including macrocycles and 1,3-enynes. Cu(bphen)(XantPhos)BF4 could also be employed in a tandem ATRA/photoisomerization process employing arylsulfonyl chlorides, an example of photoisomerization with halide-substituted olefins.

Phosphine Evaluation on a New Series of Heteroleptic Copper(I) Photocatalysts with dpa Ligand [Cu(dpa)(P,P)]BF4

Five new heteroleptic copper(I) complexes (C1-5) of the type [Cu(dpa)(P,P)]BF4 based on dipyridylamine (dpa) as N,N ligand and commercial diphosphines as P,P ancillary ligands have been synthesised through a simple methodology with high yields. All complexes were thoroughly characterised by spectroscopic and spectrometric techniques, as well by theoretical calculations. These showed Metal to Ligand Charge Transfer (MLCT) absorptions in the 300–370 nm region, and emission in the 450–520 nm region with quantum yields and lifetimes that depend on the nature of the P,P ligand. The photocatalytic performance of copper(I) complexes C1-5 was evaluated for their use as photoredox catalysts in ATRA reactions, decarboxylative coupling and an Appel-type reaction. The use of readily available dpa as N,N ligand constitutes an attractive alternative to the well-established phenanthroline ligands typically used in photocatalysis.

Hydrogen bonding network assisted regio- and stereo- controlled hydrohalogenations of sulfonyl alkynes

We have developed an efficient synthesis of β-halo Z-sulfonyl alkenes via hydrohalogenations of readily available sulfonyl alkynes. The high hydrogen bonding acidity of linear acetic acid network or aggregate may play a vital role in activation of sulfony

Iron(III) Chloride-Mediated Regio- and Stereoselective Chlorosulfonylation of Alkynes and Alkenes with Sodium Sulfinates

The atom-economic and one-pot regio- and stereoselective addition of sodium arenesulfinates to either alkynes or alkenes can be achieved with an iron(III) chloride hexahydrate [FeCl3?6 H2O] catalytic system to afford β-haloalkenyl and β-chloroalkyl sulfones in moderate to good yields. (Figure presented.).

Copper(II)-Catalyzed Chemo- and Stereocontrolled Synthesis of (E)-Vinyl Sulfones and (Z)-β-Chlorovinyl Sulfones from Terminal Alkynes and Arylsulfonyl Hydrazides

A facile copper(II)-catalyzed regio- and stereocontrolled synthesis of vinyl sulfones from terminal alkynes and arylsulfonyl hydrazides is described. Depending on the source of copper(II), two different kinds of vinyl sulfones, (E)-vinyl sulfones and (Z)-β-chlorovinyl sulfones were obtained and the addition of cyclohexanone played an important role in the reaction. These reactions display excellent chemoselectivity as well as stereoselectivity.

A method of preparing beta-chloroalkenyl sulfone compounds from sulfonates and alkynes

A method of preparing beta-chloroalkenyl sulfone compounds from sulfonates and alkynes is provided. The method includes directly synthesizing the beta-chloroalkenyl sulfone compounds from the sulfonates and the alkynes in a nitrogen or inert gas atmosphere by using an iron halogenide agent. The method adopts raw materials and the iron halogenide agent which are cheap, stable and easily available, and does not use ligands, acids, peroxides, microwave radiation, and other special reaction conditions. Pre-functionalization of a substrate is not needed. The method is mild in reaction conditions, simple in operation, short in reaction time and high in product selectivity, substrate applicability and yield, and has a potential application prospect in the fields of medicines, organic synthesis intermediates, and the like.

Aerobic copper-catalyzed synthesis of (E)-alkenyl sulfones and (E)-β-halo-alkenyl sulfones via addition of sodium sulfinates to alkynes

Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the reaction using CuI catalyst produced (E)-β-haloalkenyl sulfones anti-selectively in the presence of potassium halides. Furthermore, the (E)-β-bromoalkenyl sulfones are possible to convert into various alkenyl sulfones by Suzuki-Miyaura coupling.

Iron halide-mediated regio- and stereoselective halosulfonylation of terminal alkynes with sulfonylhydrazides: Synthesis of (E)-β-chloro and bromo vinylsulfones

Halosulfonylation of terminal alkynes was achieved with sulfonylhydrazides as the sulfonyl precursor and inexpensive iron halide as halide source in the presence of TBHP, allowing the regio- and stereoselective generation of (E)-β-chloro and bromo vinylsu

Iron-catalyzed regio- and stereoselective chlorosulfonylation of terminal alkynes with aromatic sulfonyl chlorides

Terminal alkynes react with aromatic sulfonyl chlorides in the presence of an iron(II) catalyst and a phosphine ligand to give (E)-β- chlorovinylsulfones with 100% regio- and stereoselectivity. Various functional groups, such as chloride, bromide, iodide, nitro, ketone, and aldehyde, are tolerated under the reaction conditions. Addition of tosyl chloride to a 1,6-enyne followed by radical 5-exo-trig cyclization gave an exocyclic alkenylsulfone.

Stereoselective synthesis of (Z)-β-chlorovinyl sulfones by addition of sulfonyl chlorides to acetylenes

The addition reaction of sulfonyl chlorides with acetylenes in the presence of a copper salt is described. The reaction proceeds in toluene in the presence of CuCl with Me2S as the additive to afford only (Z)-β-chlorovinyl sulfones in moderate to excellent yields. Georg Thieme Verlag Stuttgart.