70312-74-2

Usage

Molecular weight

314.42 g/mol

Type of compound

Sulfonyl styrene derivative

Structure

Contains a sulfonyl group attached to a diphenylethenyl group and a 4-methylbenzene group

Applications

a. Organic synthesis
b. Medicinal chemistry
c. Building block for biologically active molecules
d. Intermediate for polymers, pharmaceuticals, and agrochemicals

Potential

a. Exhibits a wide range of biological activities
b. Possible applications in the development of new drugs

Upstream product

• 18523-73-4 2,2-diphenylethenyl p-tolyl sulfide 
• 530-48-3 1,1-Diphenylethylene 
• 1950-78-3 p-toluenesulfonyl iodide 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 67341-86-0 Ph₂CCHHgBr 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 102478-11-5 2,2-diphenylvinyl 4-methylbenzenesulfonate 
• 103-67-3 benzyl-methyl-amine 
• 19816-85-4 N'-(1,2-diphenylethylidene)-4-methylbenzenesulfonohydrazide 
• 33757-46-9 8-(N-propionylamino)quinoline 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 536-74-3 phenylacetylene 

Downstream Products

• 211929-53-2 (2-tosylethane-1,1-diyl)dibenzene 

Relevant academic research and scientific papers

Carbomagnesiation of acetylenic sulfones catalyzed by CuCN and its application in the stereoselective synthesis of polysubstituted vinyl sulfones

Polysubstituted vinyl sulfones were prepared stereoselectively by the carbomagnesiation of acetylenic sulfones in the presence of Cu(I). Bisubstituted vinyl sulfones were obtained by the carbomagnesiation of acetylenic sulfones followed by hydrolysis. Tri

Mn(III)-promoted synthesis of spiroannular tricyclic scaffolds via sulfonylation/dearomatization of biaryl ynones

A Mn(III)-promoted radical oxidative ipso-annulation reaction of biaryl ynones with sodium sulfinates to construct various substituted spiro[5.5]trienones has been explored in this study. This protocol is characterized by mild reaction conditions, good su

Remote C-H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling

Achieving site selectivity in carbon-hydrogen (C-H) functionalization reactions is a formidable challenge in organic chemistry. Herein, we report a novel approach to activating remote C-H bonds at the C5 position of 8-aminoquinoline through copper-catalyzed sulfonylation under mild conditions. Our strategy shows high conversion efficiency, a broad substrate scope, and good toleration with different functional groups. Furthermore, our mechanistic investigations suggest that a single-electron-transfer process plays a vital role in generating sulfonyl radicals and subsequently initiating C-S cross-coupling. Importantly, our copper-catalyzed remote functionalization protocol can be expanded for the construction of a variety of chemical bonds, including C-O, C-Br, C-N, C-C, and C-I. These findings provide a fundamental insight into the activation of remote C-H bonds, while offering new possibilities for rational design of drug molecules and optoelectronic materials requiring specific modification of functional groups.

Visible-Light Photoredox-Catalyzed Sulfonyl Lactonization of Alkenoic Acids with Sulfonyl Chlorides for Sulfonyl Lactone Synthesis

A visible-light photoredox-catalyzed sulfonyl lactonization of unsaturated carboxylic acids with sulfonyl chlorides is described. This reaction features good functional group tolerance and a broad substrate scope, providing a simple and efficient protocol to access a wide range of sulfonyl lactones in high to excellent yields. Preliminary mechanistic investigations suggested that a free-radical pathway should be involved in the process.

Metal-Free Synthesis of (E)-Vinyl Sulfones via An Insertion of Sulfur Dioxide/1,5-Hydrogen Atom Transfer Sequence

A metal-free three-component reaction of propargyl alcohols, sodium metabisulfite, and aryldiazonium tetrafluoroborates under mild conditions is described. The reaction proceeds efficiently at room temperature without the need of any catalysts, affording the corresponding (E)-vinyl sulfones in moderate to good yields with excellent functional group tolerance. Preliminary mechanistic studies show that a vinyl radical-induced 1,5-hydrogen atom transfer process and functional group migration are involved, resulting in the cleavage of inert C?H and C?C bonds in sequence. (Figure presented.).

Copper(II)-catalyzed remote sulfonylation of aminoquinolines with sodium sulfinates: Via radical coupling

The efficient remote sulfonylation of N-(quinolin-8-yl)benzamide derivatives at the C5 position has been well developed. The reaction generates environmentally benign byproducts by utilizing stable and safe sodium sulfinates as sulfide sources. A series of N-(5-(phenylsulfonyl)quinolin-8-yl)benzamide derivatives were successfully obtained in moderate to high yields. In particular, they are less unpleasantly odorous and more environmentally friendly than previous means.

Photoinduced intramolecular carbosulfonylation of alkynes: access to sulfone-containing dibenzazepines from sulfur dioxide

A photoinduced three-component reaction ofN-benzyl-N-(2-ethynylaryl)amides, sulfur dioxide and aryldiazonium tetrafluoroborates is developed, providing an efficient and straightforward approach for the synthesis of diverse vinylsulfonylated dibenzazepine derivatives in moderate to good yields under mild conditions. This transformation proceeds smoothly at room temperature in the presence of visible light, which shows a wide range of substrate scope with good functional group compatibility. The synthetic utility of this methodology is further demonstrated through Suzuki coupling. Mechanistic studies show that this reaction is triggered by the addition of an arylsulfonyl radical to an alkyne from sulfur dioxide, followed by vinyl radical cyclization to afford the desired sulfonated dibenzazepines.

Directing-Group-Assisted C(sp2)-H Arylsulfonylation from Sulfur Dioxide

A straightforward and stereoselective preparation of (Z)-β-alkenyl sulfones through a reaction of N-tosyl acrylamides, 1,4-diazabicyclo[2.2.2]octane-sulfur dioxide, and aryldiazonium tetrafluoroborates under copper catalysis is accomplished. The direct C(sp2)-H arylsulfonylation of acrylamides using sulfur dioxide as the sulfonyl source in the presence of copper trifluoroacetate proceeds smoothly, giving rise to (Z)-β-alkenyl sulfones in good yields. During the reaction process, excellent regio- A nd stereoselectivities are observed.

Electrochemical Alkynyl/Alkenyl Migration for the Radical Difunctionalization of Alkenes

An efficient electrochemical 1,2-sulfonylation/alkynylation of alkenes via radical 1,4-alkynyl migration of alkynyl-substituted tertiary alcohols is described, which used sodium sulfinates as sulfonyl sources affording the corresponding α-sulfonyl-β-alkynylated products in moderate to excellent yields. This electrochemical reaction proceeds smoothly without the use of any metal catalyst, additive and oxidant and thus represents a new and eco-friendly strategy for the difunctionalization of unactive olefins, and also the first example of the electrochemical distal radical migration reaction.

Oxidant- And Catalyst-Free Synthesis of Sulfonated Benzothiophenes via Electrooxidative Tandem Cyclization

A green and practical electrochemical method for the synthesis of C-3-sulfonated benzothiophenes from 2-alkynylthioanisoles and sodium sulfinates was developed under oxidant- and catalyst-free conditions. Moderate to good yields of sulfonated benzothiophenes bearing important and useful functional groups have been achieved at a constant current. Preliminary mechanistic studies indicated a tandem radical addition-cyclization pathway. Moreover, the protocol is easy to scale up and exhibits good reaction efficiency.