30166-84-8

Usage

Chemical class

Organic sulfonyl compounds

Physical form

White to off-white solid

Molecular weight

320.41 g/mol

Common uses

Building block in organic synthesis, reagent in chemical reactions, production of pharmaceuticals and agrochemicals

Handling precautions

May pose health and environmental risks if not used properly.

Upstream product

• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 63735-42-2 sodium naphthalen-2-ylsulfinate 
• 100-42-5 styrene 
• 10151-46-9 2-naphthylsulfonyl hydrazide 
• 140-10-3 (E)-3-phenylacrylic acid 
• 637-44-5 phenylpropyolic acid 
• 621-82-9 Cinnamic acid 
• 5153-67-3 nitrostyrene 
• 132857-39-7 4-chlorophenyl naphthalene-2-sulfonate 
• 91-60-1 2-Naphthalenethiol 
• 124790-88-1 N'-(naphthalen-2-ylsulfonyl)naphthalene-2-sulfonohydrazide 
• 100-41-4 ethylbenzene 
• 93326-71-7 1-(2-naphthalenesulfonyl)benzimidazole 
• 93-11-8 2-Naphthalenesulfonyl chloride 

Relevant academic research and scientific papers

Copper-Catalyzed Heck-Type Couplings of Sulfonyl Chlorides with Olefins: Efficient and Rapid Access to Vinyl Sulfones

A copper-catalyzed redox-neutral alkene sulfonylation reaction has been developed. This reported protocol can be easily scale up to a gram scale, and smoothly applied to the late-stage modification of several bioactive molecules.

Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones

A photocatalyst-free visible light mediated decarboxylative sulfono functionalization protocol has been explored for the synthesis of (E)-vinyl sulfones from cinnamic acids and bench-stable arylazo sulfones. The latter have been utilized as sulfonyl radic

Cu-catalyzed dehydrogenative olefinsulfonation of Alkyl arenes

A copper-catalyzed reaction protocol for the dehydrogenation of ethylbenzenes into styrene derivatives has been developed. This reaction procedure proceeded well under mild reaction conditions, providing a practical and efficient strategy for the rapid assembly of biologically and pharmaceutically significant molecules, such as vinyl sulfone. Simple alkyl arenes were functionalized via consecutive β-elimination in the presence of N-sulfonylbenzo[d]imidazole with broad substrate scope and good functional group tolerance.

Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: A metal- And oxidant-free protocol for the synthesis of (: E)-vinyl sulfones in water

An efficient electrochemical transformation of a variety of alkenes and sulfonyl hydrazides into vinyl sulfones with a catalytic amount of tetrabutylammonium iodide in water is reported. The reaction proceeds smoothly to afford vinyl sulfones with good selectivities and yields at room temperature under air in an undivided cell. Cyclic voltammograms and control experiments have been performed to provide preliminary insight into the reaction mechanism. The key features of this reaction include using pure water as solvent, transition metal- and oxidant-free conditions, and being easily scaled up to gram-scale synthesis. This journal is

N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature

N,N′-Disulfonylhydrazines have been proven to be the most reactive precursors of sulfonyl radicals in all types of sulfonyl substituted hydrazines as early as a half century ago. But such function has not been applied in organic synthesis except the formation of disulfones by self-dimerization of sulfonyl radicals. In this article, they were introduced as new sulfonylating reagents and their combinations with NIS and Et3N were established as excellent iodosulfonylating reagents for alkenes. Finally, a highly efficient method for the synthesis of (E)-vinyl sulfones was developed by mixing an alkene, a N,N′-disulfonylhydrazine, NIS and Et3N in THF at room temperature for 5 min.

Electron Donor-Acceptor Complex Enabled Decarboxylative Sulfonylation of Cinnamic Acids under Visible-Light Irradiation

Visible-light-induced decarboxylative sulfonylation of cinnamic acids with aryl sulfonate phenol esters enabled by the electron donor-acceptor complex is developed. The method offers a mild and green approach for the synthesis of vinyl sulfones with excellent functional group compatibility under photocatalyst and oxidant-free conditions.

Visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates by using Merrifield resin supported Rose Bengal as a catalyst

A visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates for the synthesis of vinyl sulfones was developed. The reaction proceeded smoothly in the presence of Merrifield resin supported Rose Bengal ammonium salt as a

Aerobic Copper-Catalyzed Synthesis of (E)-Vinyl Sulfones by Direct C-S Bond Oxidative Coupling

Copper-catalyzed aerobic oxidative C-S bond coupling reaction between thiophenols and aryl-substituted alkenes for (E)-vinyl sulfones synthesis is reported here. With air utilized as a green oxidant, this transformation not only produces various vinyl sulfones in moderate to good yields but also possesses a simple and ecofriendly system. To clarify the mechanism, kinetic experiments has been investigated.

Synthetic method of (E)-alkenyl sulfone compounds

The invention discloses a synthetic method of (E)-alkenyl sulfone compounds. The method comprises the following steps: beta-nitroolefin compounds shown as formula I in the description, sulfohydrazidecompounds shown as formula II in the description, an iodine-containing nonmetal catalyst and a peroxide oxidizing agent are mixed for a reaction, and a mixture obtained after the reaction is subjectedto postprocessing, and the (E)-alkenyl sulfone compounds shown as formula III in the description are obtained. Beta-nitroolefin compounds, the sulfohydrazide compounds, the iodine-containing nonmetalcatalyst and the peroxide oxidizing agent are taken as main raw materials, the corresponding (E)-alkenyl sulfone compounds are synthesized through free radical reaction, the iodine-containing nonmetal catalyst iodine or tetrabutylammonium iodide is used, the raw materials are simple, easily available, cheap, non-toxic and pollution-free to the environment, the dosage of the catalyst is small, thecatalyst has higher specificity for the reaction, synthetic reaction time can be shortened, the problem that the metal catalyst is difficult to separate in the prior art can be well solved, postprocessing difficulty is reduced, yield of the final product is increased, and purity of the final product is improved.

(E)-alkenyl sulfone compound and preparation method thereof

The present invention relates to a (E)-alkenyl sulfone compound and a preparation method thereof. The preparation method comprises: dissolving a benzenesulfonyl hydrazide-based substrate and a phenylpropiolic acid substrate in an organic solvent, adding a