1237801-80-7

Upstream product

• 1746-23-2 4-tert-Butylstyrene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 220006-53-1 3-(4-(tert-butyl)phenyl)propiolic acid 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 98-59-9 p-toluenesulfonyl chloride 
• 14062-05-6 N,N'-ditosylhydrazine 
• 772-38-3 4-tert-Butylphenylacetylene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1208-65-7 3-(4-(tert-butyl)phenyl)acrylic acid 

Relevant academic research and scientific papers

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

Iodine-mediated synthesis of (E)-vinyl sulfones from sodium sulfinates and cinnamic acids in aqueous medium

With water as the reaction medium, a green and efficient method has been developed for the synthesis of (E)-vinyl sulfones via I2-mediated decarboxylative cross-coupling reactions of sodium sulfinates with cinnamic acids. This synthetic route could effectively avoid the use of toxic organic solvents and transition metal catalysts, and the target products could be obtained with moderate to excellent yields under green and mild conditions.

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.

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.

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.].

Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent

A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and β-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.

Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study

A variety of vinyl sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and with small surface area electrodes. A possible reaction mechanism was proposed with the use of cyclic voltammetry. It is the combination of anodic and cathodic processes in this reaction that makes it possible to obtain products under mild conditions with yields from moderate to high.

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.

An efficient and facile synthesis of vinyl sulfones via microwave-assisted copper triflate catalyzed hydrosulfonylation of alkynes

An efficient method has been described for the synthesis of vinyl sulfones via hydrosulfonylation of alkynes using sodium arene sulfinates catalyzed by Cu(OTf)2 under microwave irradiation. A variety of vinyl sulfones was obtained in good to ex

Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers

A regio- and stereoselective synthesis of sulfones and thioethers by means of CuI-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C-sp-2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry. First cleave, then cross-couple: A direct Cu-catalyzed aerobic oxidative C-sp-2-H functionalization and C-S bond coupling reaction has been developed (see scheme). By slight modification of the additive, sulfonyl hydrazides could serve as sulfonation, sulfenation, or arylation reagents to undergo cross-coupling reactions with alkenes and (hetero)aromatic cycles, affording sulfones, thioethers, and biaryl compounds with high regio- and stereoselectivities (see scheme).