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Relevant academic research and scientific papers

A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides

A ruthenium-catalysed cross-olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.

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.

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 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.

One-pot synthesis method of (Z)-type sulfonyl olefine acid ester compound

The invention discloses a one-pot synthesis method of a (Z)-type sulfonyl olefine acid ester compound. According to the method, the sulfonyl olefine acid ester compound is obtained by one-pot reaction of a sulfinic acid sodium and an acetylenic acid ester

Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature

On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β-ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors. It's all happenin' in the micelle! The highly preferential dissolution of oxygen gas within the lipophilic cores inside nanomicelles leads to efficient trapping of in situ generated vinyl radicals. These intermediate radicals, derived from arylalkynes and sulfinic acids, lead to β-ketosulfone products, formed under especially mild and green conditions: no metals, no heating or cooling, recyclable aqueous media, and low E Factors.

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

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.

Unexpected transfer of tosyl group of ArCH=NTs-catalyzed by N-heterocyclic carbene

(Chemical Equation Presented) Reactions of N-tosylimines with aziridines and electron-deficient unsaturated compounds in the presence of catalytic amount of NHC afforded unexpected tosyl group transfer products in good to high yields, which represent a new reaction pattern for imines as well as for catalysis of NHC.