10154-75-3Relevant articles and documents
1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane as new oxidant for chemoselective and catalyst free oxidation of sulfides to sulfoxides and sulfones
Khosravi, Kaveh,Naserifar, Shirin,Mahmoudi, Boshra,Khalaji, Kobra
, p. 316 - 321 (2017)
A catalyst free and chemoselective oxidation of sulfides to sulfoxides or sulfones was developed using 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as a new oxidant. This scope has shown the achievement of various sulfoxides and sulfones which were obtained selectively in high yields at room temperature.
Preparation method of alkyl nitrile compound
-
Paragraph 0195-0197; 0205-0207, (2020/08/18)
The invention discloses a preparation method of an alkyl nitrile compound. Specifically, the preparation method comprises the following step: in an organic solvent, in the presence of a protective gasand under the action of a catalyst, carrying out a reduction reaction as shown in the specification on olefin as shown in a formula I, a cyanation reagent and water, wherein the alkyl nitrile compound 1 is a compound II and/or a compound III. The preparation method provided by the invention is mild in condition, can realize hydrocyanation of olefin more safely and efficiently, and has good substrate universality and functional group compatibility.
Radical cyanomethylation via vinyl azide cascade-fragmentation
Donald, James R.,Berrell, Sophie L.
, p. 5832 - 5836 (2019/06/17)
Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.
Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant
Kupwade,Khot,Lad,Desai,Wadgaonkar
, p. 6875 - 6888 (2017/10/06)
Abstract: We describe here our journey from the failure of our attempts in controlled oxidation of sulfides to sulfoxides using an Oxone–KBr combination to our success in the development of a catalyst-free protocol for the oxidation of sulfides to sulfoxides using Oxone as an oxidant. We also describe the failure of our attempts at the oxidation of sulfides to sulfones using an excess of Oxone–KBr as well as Oxone, and our success towards the development of a rapid, scalable and chromatography-free protocol for the oxidation of sulfides to sulfones using diethylamine–Oxone as an unprecedented catalyst–oxidant combination.
Synthesis of alkyl aryl sulfones via reaction of N-arylsulfonyl hydroxyamines with electron-deficient alkenes
Bin, Yunhui,Hua, Ruimao
, (2017/01/24)
Alkyl aryl sulfones were prepared in high yields via the reaction of N-arylsulfonyl hydroxylamines with electron-deficient alkenes. These reactions have the advantages of simplicity, easily available starting materials and mild reaction conditions.
Catalyst-free synthesis of 3-sulfone nitrile from sulfonyl hydrazides and acrylonitrile in water
Li, Wei,Gao, Lingfeng,Zhuge, Wenyun,Sun, Xu,Zheng, Gengxiu
, p. 7819 - 7823 (2017/10/06)
A novel catalyst-free sulfonation reaction for synthesizing 3-sulfone nitrile compounds from sulfonyl hydrazides and acrylonitriles in water, without any metal catalyst, ligand or organic solvent, was demonstrated. This catalyst-free protocol provides a new synthetic method for the construction of 3-sulfone nitrile compounds with excellent yields. The D2O experiment adequately proved that the catalyst-free sulfonation reaction occurs via a Michael addition mechanism and that the hydrogen of 3-sulfone nitrile comes from water.
Deep Eutectic Solvents as Reaction Media for the Palladium-Catalysed C?S Bond Formation: Scope and Mechanistic Studies
Marset, Xavier,Guillena, Gabriela,Ramón, Diego J.
supporting information, p. 10522 - 10526 (2017/08/10)
A unique jigsaw catalytic system based on deep eutectic solvents and palladium nanoparticles where C?S bonds are formed from aryl boronic acids and sodium metabisulfite, is introduced. The functionalization step is compatible with a broad spectrum of reagents such as nucleophiles, electrophiles or radical scavengers. This versatile approach allows the formation of different types of products in an environmentally friendly medium by selecting the components of the reaction, which engage one with another as pieces in a jigsaw. This simple procedure avoids the use of toxic volatile organic solvents allowing the formation of complex molecules in a one-pot reaction under mild conditions. Despite the fact that only 1 mol % of metal loading is used, the recyclability of the catalytic system is possible. Kinetic experiments were performed and the reaction order for all reagents, catalyst and ligand was determined. The obtained results were compared to palladium nanocrystals of different known shapes in order to shed some light on the properties of the catalyst.
Method for synthesizing 3-sulfonyl nitrile compound
-
Paragraph 0012, (2017/04/03)
The invention discloses a method for synthesizing a 3-sulfonyl nitrile compound. The method includes the steps of using substituted sulfonhydrazide and an acrylonitrile compound as raw materials for a reaction in water by heating to obtain the 3-sulfonyl nitrile compound, and after the reaction, obtaining the 3-sulfonyl nitrile compound with a purity of 95% or above by simple separation. Compared with other synthetic methods, the method is simpler in reaction step, more environmentally friendly in synthesis and higher in yield. Important nitrile pharmaceutical chemical intermediates are directly synthesized by one step, and a novel method is provided for synthesizing the sulfonyl-substituted nitrile compound for the field of chemical synthesis.
A chemoselective oxidation of sulfides to sulfoxides and sulfones using urea-2,2-dihydroperoxypropane as a novel oxidant
Khosravi, Kaveh,Naserifar, Shirin,Asgari, Atefeh
, p. 749 - 756 (2017/02/05)
Background: Sulfoxides and sulfones have been in the center of attention due to their wide range of promises in various approaches. The functional groups presented in these compounds serve as important building blocks in numerous natural, pharmeceutical and agricultural compounds. These deriatives have been prepared through a multitude of routes which were accompanied by several drawbacks. Therefore, there has been an ever-increasing interest to find a new methodology that leads to the production of these compounds via an environmentally benign path bringing about high yields. Recently, gem-dihydroperoxides have attracted much attention due to their oxidizing power and they have been utilized in several oxidation processes. Methods: We carried out a chemoselective oxidation of sulfides to sulfoxides and sulfones on treatment with urea-2,2-dihydroperoxypropane, a solid oxidant composed of equal amounts of 2,2-dihydroperoxypropane and urea, using THF as the solvent under catalyst-free conditions at room temprature. Results: Sulfides possessing a variety of substitutions namely dialkyl, diaryl, ally l and alkyl-aryl were subjected to the optimized reaction conditions and they could successfully afford different amounts of sulfoxides and sulfones depending on the amount of the oxidant utilized. Based on the results, electron-donating groups accelerated the reaction while electron-withdrawing substituents lowered the reactivity. Conclusion: Urea-2,2-dihydroperoxypropane as a solid oxidant which can be stored for several months without any loss in its activity has proved its capability to oxidize sulfides to sulfoxides and sulfones under catalyst-free and mild conditions. This approach is a cost-effective and environmentally benign methodology via which the products have been synthesized in high yields and short reaction times.
Method for preparing substituted ethyl aryl sulfone
-
Paragraph 0058-0059, (2017/03/23)
The invention discloses a method for preparing substituted ethyl aryl sulfone. The method comprises the following steps: a compound shown in a formula II, a compound shown in a formula III and alkali are uniformly mixed in a solvent and are subjected to a coupling reaction, a compound shown in a formula I containing R2' as -CH2CH2R is obtained after the reaction is complete; or the method comprises the following steps: the compound shown in the formula II, ethyl propiolate and alkali are uniformly mixed in the solvent and then are subjected to the coupling reaction, and the compound shown in a formula I containing R2' as -CH=CH2=OOCH2CH3 is obtained after the reaction is complete. The method has the advantages of universality, convenience, simple reaction system, and mild reaction condition; the reaction can be amplified to a gram level, the reaction raw materials are simple and easily available, the used alkali and raw materials have the advantages of low cost and easy acquisition, the atom utilization rate is high, and solvent toxicity is low.
