1402459-57-7

Upstream product

• 369-51-7 4-fluorobenzenesulfinic acid 
• 623-47-2 propynoic acid ethyl ester 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 2266-41-3 4-fluorobenzenesulfonylhydrazide 
• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 1260427-50-6 (Z)-ethyl 3-((4-fluorophenyl)thio)acrylate 
• 371-42-6 4-Fluorothiophenol 

Relevant academic research and scientific papers

Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation

Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered for radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox-catalyzed hydrosulfonylation of electron-deficient alkenes with sulfonyl chlorides. To increase the generality of this transformation, polarity-reversal catalysis (PRC) was successfully implemented for alkenes bearing alkyl substituents. This late-stage functionalization method tolerates a remarkably wide range of functional groups, is operationally simple, scalable, and allows access to building blocks which are important for medicinal chemistry and drug discovery.

Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water

We report the atom-economic and environmentally friendly synthesis of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds in water. The mechanism study reveals that the hydrosulfonylation of alkynylcarbonyl compounds with sulfinic acids proceeds via a mechanism that features a sulfinic acid molecule protonating an alkynyl motif to form the ethenium intermediate, which subsequently reacted with a sulfonyl anion to afford the desired products. The ethenium intermediate differentiated electronic and steric demands between the two substituents on the C≡C triple bond of the alkyne substrates to exhibit high regio- and stereoselectivity from a wide range of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds.

A (Z)-sulfonyl dibutyl ester preparation method (by machine translation)

This invention relates to a kind of (Z)-sulfonyl dibutyl ester preparation method, the method is the ester compound acetylenic acid[...] compound and through the one-pot synthesis generating addition-elimination reaction, to obtain sulfonyl dibutyl ester; under mild conditions of the method, by one-pot reaction, high yield, high selectivity synthesis of (Z)-type sulfonyl enoic acid ester compound, and the operation is simple, environment friendly, and without need to add the catalyst, which is beneficial for industrial production. (by machine translation)

A direct catalyst-free and stereoselective sulfonylation of propargyl esters for efficient synthesis of (Z)-β-sulfonyl enoates in water

Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of (Z)-β-sulfonyl enoates in excellent yields, by a simple, mild, and environmentally benign reaction procedure without employing any ligand or additive is reported.

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.

A Mild and Rapid Synthesis of (Z)-β-Sulfonyl Enoates from Sodium Sulfinates and Propargyl Esters

Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of (Z)-β-sulfonyl enoates in excellent yields, by a simple, mild, rapid and environmentally benign reaction procedure is reported.

One-pot three-step thioconjugate addition-oxidation-Diels-Alder reactions of ethyl propiolate

Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels-Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.

One-pot synthesis of (Z)-β-sulfonyl enoates from ethyl propiolate

β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from ethyl propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of ali