10154-71-9Relevant academic research and scientific papers
Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism
Zhang, Wen,Lin, Song
supporting information, p. 20661 - 20670 (2020/12/23)
Electrochemistry grants direct access to reactive intermediates (radicals and ions) in a controlled fashion toward selective organic transformations. This feature has been demonstrated in a variety of alkene functionalization reactions, most of which proceed via an anodic oxidation pathway. In this report, we further expand the scope of electrochemistry to the reductive functionalization of alkenes. In particular, the strategic choice of reagents and reaction conditions enabled a radical-polar crossover pathway wherein two distinct electrophiles can be added across an alkene in a highly chemo- and regioselective fashion. Specifically, we used this strategy in the intermolecular carboformylation, anti-Markovnikov hydroalkylation, and carbocarboxylation of alkenes - reactions with rare precedents in the literature - by means of the electroreductive generation of alkyl radical and carbanion intermediates. These reactions employ readily available starting materials (alkyl halides, alkenes, etc.) and simple, transition-metal-free conditions and display broad substrate scope and good tolerance of functional groups. A uniform protocol can be used to achieve all three transformations by simply altering the reaction medium. This development provides a new avenue for constructing Csp3-Csp3 bonds.
Multicomponent Synthesis of Sulfones and Sulfides from Triarylbismuthines and Sodium Metabisulfite in Deep Eutectic Solvents
Saavedra, Beatriz,Marset, Xavier,Guillena, Gabriela,Ramón, Diego J.
supporting information, p. 3462 - 3467 (2020/06/04)
This study describes a novel and catalyst-free methodology for the multicomponent synthesis of a broad range of sulfones, disulfides, and sulfides from non-toxic triarylbismuthines (Ar3Bi) and sodium metabisulfite (Na2S2O5) in deep eutectic solvents (DESs). The fine tuning of the DESs properties allowed the solubility of all reagents, enhancing their reactivity, as well as, the recyclability of the reaction medium for at least 5 consecutive cycles. Thus, this versatile strategy uses non-toxic reagents without the need of metal catalysts in a sustainable solvent, being an interesting alternative to traditional hazardous protocols.
Synthetic method of 3-(benzenesulfonyl) propionic acid
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Paragraph 0029-0043, (2019/07/04)
The invention discloses a synthetic method of 3-(benzenesulfonyl) propionic acid. The synthetic method has the benefits that sodium benzene sulphinate and maleic anhydride are taken as raw materials,and the 3-(benzenesulfonyl) propionic acid is synthesize
Synthesis method of 3-sulfonyl propionic acid compound
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Paragraph 0016, (2017/08/28)
The invention discloses a synthesis method of a 3-sulfonyl propionic acid compound. The method comprises the following steps: performing reaction by taking substituent sulfonhydrazide and alpha, beta-unsaturated carboxylic acid compounds as raw materials and water as a solvent to produce 3-sulfonyl propionic acid, and performing simple separation after the reaction to obtain the 3-sulfonyl propionic acid. According to the method, the 3-sulfonyl propionic acid can be obtained through one-step reaction, the solvent is environmentally-friendly and the yield is high. The propionic acid compound obtained by one-step direct synthesis is an important medical intermediate, a new method for synthesizing sulfonyl substituent carboxylic acid compound is provided for the field of chemical synthesis.
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.
Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B
Grove, Charles I.,Di Maso, Michael J.,Jaipuri, Firoz A.,Kim, Michelle B.,Shaw, Jared T.
supporting information, p. 4338 - 4341,4 (2012/12/11)
Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.
Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B
Grove, Charles I.,Di Maso, Michael J.,Jaipuri, Firoz A.,Kim, Michelle B.,Shaw, Jared T.
supporting information, p. 4338 - 4341 (2013/01/14)
Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.
Design of potent inhibitors of human β-secretase. Part 1
Freskos, John N.,Fobian, Yvette M.,Benson, Timothy E.,Bienkowski, Michael J.,Brown, David L.,Emmons, Thomas L.,Heintz, Robert,Laborde, Alice,McDonald, Joseph J.,Mischke, Brent V.,Molyneaux, John M.,Moon, Joseph B.,Mullins, Patrick B.,Bryan Prince,Paddock, Donna J.,Tomasselli, Alfredo G.,Winterrowd, Gregory
, p. 73 - 77 (2007/10/03)
We describe a novel series of potent inhibitors of human β-secretase. These compounds possess the hydroxyethyl amine transition state isostere. A 2.5 A crystal structure of inhibitor 32 bound to BACE is provided.
A structure-taste study of arylsulfonyl(cyclo)alkanecarboxylic acids
Lysiak, Violetta,Ratajczak, Aleksander,Mencel, Agnieszka,Jarzembek, Krystyna,Polanski, Jaroslaw
, p. 671 - 675 (2007/10/03)
A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds.
