56759-30-9

Upstream product

• 1945-84-2 2-ethynylpyridine 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 100-69-6 2-vinylpyridine 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 14062-05-6 N,N'-ditosylhydrazine 
• 54765-14-9 2‐(pyridin‐2‐yl)acetaldehyde 
• 54495-51-1 (E)-3-(2-pyridyl)acrylic acid 
• 106-45-6 para-thiocresol 
• 7340-22-9 3-pyridin-2-yl-acrylic acid 
• 657-84-1 sodium tosylate 

Relevant academic research and scientific papers

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.

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

Cu-doped zeolitic imidazolate framework catalysed highly selective conversion of alkynes to β -keto and vinyl sulfones using sodium sulfinates

Abstract: Cu 2 +-doped zeolitic imidazolate framework-8 (ZIF-8)-catalyzed one-pot procedure to synthesize β -keto and vinyl sulfones by the direct oxysulfonylation and hydrosulfonylation of alkynes via radical reaction under mild conditions has been described. The advantages of this protocol included broad substrate scope and excellent β -keto and E-stereoselectivity. The Cu/ZIF-8 catalyst not only exhibited excellent performance but also had a great stability in the reaction, successfully allowing its reuse up to five cycles. This efficient Cu/ZIF-8 heterogeneous catalyst is explored for the first time to generate β -keto and vinyl sulfones. Graphical Abstract:: Cu 2 +-doped zeolitic imidazolate framework-8 (ZIF-8)-catalyzed one-pot procedure to synthesize β -keto and vinyl sulfones by the direct oxysulfonylation and hydrosulfonylation of alkynes via radical reaction under mild conditions is described. The advantages of this protocol included broad substrate scope and excellent β -keto and E-stereoselectivity. This efficient Cu/ZIF-8 heterogeneous catalyst is explored for the first time for C-S bond formation. [Figure not available: see fulltext.].

Gram-scale synthesis of β-sulfonyl styrenes

A simple and gram-scale synthesis of β-sulfonyl styrenes has been developed starting from one-pot PPA (polyphosphoric acid)-catalyzed 1,1-diacetoxylation of arylacetaldehydes (ArCH2CHO) with acetic anhydride (Ac2O) followed by deacetoxylative sulfonylation of the resulting 1,1-diacetate intermediate with sodium sulfinates (RSO2Na) in good yields under solvent-free conditions.

Metal-free catalyzed synthesis of the (E)-vinyl sulfones via aromatic olefins with arylsulfonyl hydrazides

Synthesis of vinyl sulfones from aromatic olefins and arylsulfonyl hydrazides via I2-TBHP catalyzed system under the N2 atmosphere is described. Owing to no use of metal, only producing N2 and water as the byproducts and d

Electrochemical Decarboxylative Sulfonylation of Cinnamic Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones

A stereoselective synthesis of (E)-vinyl sulfones has been developed via electrochemical oxidative N-S bond cleavage of aromatic sulfonylhydrazides, followed by cross-coupling reactions with cinnamic acids to form the C-S bond. The protocol proceeded smoo

Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones

A facile I2O5-mediated direct oxidative coupling of aromatic alkenes with thiols toward vinyl sulfones has been developed under metal-free conditions. This methodology provides a convenient and efficient approach to various (E)-vinyl sulfones from readily available starting materials with excellent regioselectivity. The present oxidative coupling reaction, not only expands the scope of functionalization of alkenes with thiols, but also makes it a practical and powerful complement to traditional methods for the synthesis of (E)-vinyl sulfones.

Stereoselective Synthesis of Alkenyl Silanes, Sulfones, Phosphine Oxides, and Nitroolefins by Radical C-S Bond Cleavage of Arylalkenyl Sulfides

A radical-mediated approach has been introduced for the C-S bond activation of arylalkenyl sulfides. The protocol provides an efficient approach for the generation of various alkenes including alkenyl silanes, sulfones, phosphine oxides, and nitroolefins. In most cases, these radical substitutions are performed under metal-free conditions with stereospecificity.

Regioselective and stereoselective sulfonylation of alkynylcarbonyl compounds in water

With water as the reaction medium, an efficient protocol has been developed for the synthesis of Z-β-sulfonyl-α,β-unsaturated carbonyl products via water-promoted sulfonylation of alkynylcarbonyl compounds with sodium sulfinates. This strategy could effectively avoid the use of toxic organic solvents, catalysts and additives. This method features a wide substrate scope with a broad range of functional group tolerance, utilizes easily available starting materials, can be scaled-up, and is operationally simple.

Iron/copper Co-catalyzed synthesis of vinyl sulfones from sulfonyl hydrazides and alkyne derivatives

A new approach to the selective synthesis of (E)-vinyl sulfones has been developed via a Fe/Cu co-catalyzed sulfonylation of arylpropiolic acid or phenylacetylene with sulfonyl hydrazides. A variety of vinyl sulfones have been obtained in moderate to good yields, comparable to the best results reported so far. The inexpensive Fe/Cu co-catalyzed method features a simple experimental procedure and good tolerance of substrate.