Catalytic, Enantioselective syn-Diamination of Alkenes

Journal of the American Chemical Society, Год журнала: 2019, Номер 141(48), С. 19161 - 19170

Опубликована: Ноя. 19, 2019

The enantioselective, vicinal diamination of alkenes represents one the stereocontrolled additions that remains an outstanding challenge in organic synthesis. A general solution to this problem would enable efficient and selective preparation widely useful, enantioenriched diamines for applications medicinal chemistry catalysis. In article, we describe first syn-diamination simple mediated by a chiral, organoselenium catalyst together with N,N'-bistosyl urea as bifunctional nucleophile N-fluorocollidinium tetrafluoroborate stoichiometric oxidant. Diaryl, aryl-alkyl, alkyl-alkyl olefins bearing variety substituents are all diaminated consistently high enantioselectivities but variable yields. reaction likely proceeds through Se(II)/Se(IV) redox catalytic cycle reminiscent syn-dichlorination reported previously. Furthermore, syn-stereospecificity transformation shows promise highly enantioselective diaminations no strong steric or electronic bias.

Язык: Английский

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Electrophilic Selenium-Catalyzed Desymmetrizing Cyclization to Access P-Stereogenic Heterocycles

ACS Catalysis, Год журнала: 2023, Номер 13(20), С. 13301 - 13309

Опубликована: Окт. 2, 2023

The construction of phosphorus stereocenters under metal-free conditions remains a formidable challenge. Herein, we report mechanistically distinct chiral electrophilic selenium catalysis-enabled desymmetrizing cyclization to access valuable phosphorus-stereogenic heterocycles with high efficiency. This ambient temperature method affords broad range compounds that bear phenolic hydroxyl group as useful synthetic handle and, thus, enriches the toolbox for rapid generation molecular complexity. control experiments and DFT calculations indicate dual-hydrogen-bonding bridge formed between substrate TfO– anion plays crucial role in determining enantioselectivity transformation.

Язык: Английский

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Electrochemical synthesis of selenyl-dihydrofurans via anodic selenofunctionalization of allyl-naphthol/phenol derivatives and their anti-Alzheimer activity

Organic & Biomolecular Chemistry, Год журнала: 2020, Номер 18(26), С. 4916 - 4921

Опубликована: Янв. 1, 2020

Herein, we report an eco-friendly, electrosynthetic approach for the intramolecular oxyselenylation of allyl-naphthol/phenol derivatives.

Язык: Английский

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Temperature-Controlled Chalcogenation and Chalcogenocyanation of Imidazopyridines in Water under Transition Metal-Free Conditions

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(14), С. 9106 - 9116

Опубликована: Июнь 16, 2020

A sustainable and transition metal-free approach for C3 chalcogenation chalcogenocyanation of imidazopyridines with KXCN (X = S or Se) has been developed under mild conditions. Importantly, this reaction was performed in the presence catalytic iodine aqueous medium, which afforded either chalcogenated chalcogenocyanated temperature control. The current protocol featured a broad substrate scope, organic solvent-free conditions, operational convenience, gram-scale production.

Язык: Английский

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Catalytic, Enantioselective Syn-Oxyamination of Alkenes

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(33), С. 13408 - 13417

Опубликована: Авг. 10, 2021

The chemo-, regio-, diastereo-, and enantioselective 1,2-oxyamination of alkenes using selenium(II/IV) catalysis with a chiral diselenide catalyst is reported. This method uses N-tosylamides to generate oxazoline products that are useful both as protected 1,2-amino alcohol motifs ligands. reaction proceeds in good yields excellent enantio- diastereoselectivity for variety pendant functional groups such sulfonamides, alkyl halides, glycol-protected ketones. Furthermore, the rapid generation demonstrated expeditious assembly PHOX ligands well diversely amino alcohols.

Язык: Английский

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Regio- and stereoselective electrochemical selenoalkylation of alkynes with 1,3-dicarbonyl compounds and diselenides

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(10), С. 2815 - 2820

Опубликована: Янв. 1, 2022

A regio- and stereoselective electrochemical approach for the selenoalkylation of alkynes with 1,3-dicarbonyl compounds diselenides has been developed.

Язык: Английский

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Synthesis and Applications of Organic Selenols

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(24), С. 5360 - 5385

Опубликована: Ноя. 13, 2021

Abstract The synthesis and the study of organoselenium compounds have received much attention over past decades. Selenium‐containing organic molecules are widely used in synthesis, materials science, medicinal chemistry. Selenium – more specifically amino acid selenocysteine, bearing a selenol (SeH) moiety is present at least 25 human protein families, whose biological functions not been completely identified. Amongst variety compounds, selenols versatile class easily undergoing broad array useful transformations. Because unique properties SeH group, chemistry has important applications chemical sciences, spanning from to biology. This review summarises currently available methodologies for highlights sciences magnified image

Язык: Английский

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Revealing the internal heavy chalcogen atom effect on the photophysics of the dibenzo[a,j]phenazine-cored donor–acceptor–donor triad

Journal of Materials Chemistry C, Год журнала: 2021, Номер 9(39), С. 13942 - 13953

Опубликована: Янв. 1, 2021

Donor–acceptor–donor molecules containing heavy chalcogen atoms, which feature multi-color polymorphism, external-stimuli responsive luminochromism, thermally-activated delayed fluorescence, and room-temperature phosphorescence, have been developed.

Язык: Английский

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Visible light-promoted photocatalyst-free activation of persulfates: a promising strategy for C–H functionalization reactions

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(16), С. 3249 - 3262

Опубликована: Янв. 1, 2022

This review summarizes visible light-induced photocatalyst-free C–H functionalization reactions employing persulfates. The proceeded through the generation of persulfate radical anions from persulfates under light irradiation.

Язык: Английский

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Novel water-soluble organoselenocyanates and symmetrical diselenides tethered N-succinanilate and N-maleanilate as corrosion inhibitors for reinforced steel in the simulated concrete pore solution

Construction and Building Materials, Год журнала: 2022, Номер 366, С. 130135 - 130135

Опубликована: Дек. 27, 2022

Язык: Английский

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