DMSO-catalysed late-stage chlorination of (hetero)arenes

Nature Catalysis, Год журнала: 2019, Номер 3(2), С. 107 - 115

Опубликована: Дек. 23, 2019

Язык: Английский

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Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

Chemical Reviews, Год журнала: 2020, Номер 120(20), С. 11479 - 11615

Опубликована: Сен. 24, 2020

Low molecular weight synthetic peptides have been demonstrated to be effective catalysts for an increasingly wide array of asymmetric transformations. In many cases, these peptide-based enabled novel multifunctional substrate activation modes and unprecedented selectivity manifolds. These features, along with their ease preparation, modular tunable structures, often biomimetic attributes make well-suited as chiral broad interest. Many examples peptide-catalyzed reactions appeared in the literature since last survey this field

Язык: Английский

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Seaweed Secondary Metabolites with Beneficial Health Effects: An Overview of Successes in In Vivo Studies and Clinical Trials

Marine Drugs, Год журнала: 2019, Номер 18(1), С. 8 - 8

Опубликована: Дек. 20, 2019

Macroalgae are increasingly viewed as a source of secondary metabolites with great potential for the development new drugs. In this development, in vitro studies only first step long process, while vivo and clinical trials most revealing stages true limitations that given metabolite may have drug. This literature review aims to give critical overview reveal interesting results these two steps. Phlorotannins show pharmaceutical models and, among several examples, anti-dyslipidemia activity dieckol must be highlighted because it was more effective than lovastatin an model. The IRLIIVLMPILMA tridecapeptide exhibits level similar hypotensive drug captopril should still stressed, well griffithsin which showed such stunning over variety animal will probably move onto soon. Regarding trials, pure algal scarce, limited those carried out kahalalide F fucoxanthin. majority currently aim ascertain effect algae consumption, extracts or fractions, on obesity diabetes.

Язык: Английский

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Alkene Synthesis by Photocatalytic Chemoenzymatically Compatible Dehydrodecarboxylation of Carboxylic Acids and Biomass

ACS Catalysis, Год журнала: 2019, Номер 9(10), С. 9485 - 9498

Опубликована: Сен. 9, 2019

Direct conversion of renewable biomass and bioderived chemicals to valuable synthetic intermediates for organic synthesis materials science applications by means mild chemoselective catalytic methods has largely remained elusive. Development artificial systems that are compatible with enzymatic reactions provides a synergistic solution this enduring challenge leveraging previously unachievable reactivity selectivity modes. We report herein dual dehydrodecarboxylation reaction is enabled crossover the photoinduced acridine-catalyzed O-H hydrogen atom transfer (HAT) cobaloxime-catalyzed C-H-HAT processes. The produces variety alkenes from readily available carboxylic acids. can be embedded in scalable triple-catalytic cooperative chemoenzymatic lipase-acridine-cobaloxime process allows direct plant oils long-chain terminal alkenes, precursors polymers.

Язык: Английский

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Visible‐Light‐Induced Vicinal Dichlorination of Alkenes through LMCT Excitation of CuCl₂

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(52), С. 23603 - 23608

Опубликована: Сен. 14, 2020

Abstract This work demonstrates photoredox vicinal dichlorination of alkenes, based on the homolysis CuCl 2 in response to irradiation with visible light. catalysis proceeds via a ligand metal charge transfer process and provides an exciting opportunity for synthesis 1,2‐dichloride compounds using inexpensive, low‐molecular‐weight chlorine source. new exhibits wide substrate scope, excellent functional group tolerance, extraordinarily mild conditions does not require external ligands. Mechanistic studies show that ready formation atom radicals is responsible facile C−Cl bonds this synthetic process.

Язык: Английский

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Recent advances in indoline synthesis

Tetrahedron, Год журнала: 2019, Номер 75(14), С. 2063 - 2097

Опубликована: Фев. 10, 2019

Язык: Английский

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Seaweed Secondary Metabolites In Vitro and In Vivo Anticancer Activity

Marine Drugs, Год журнала: 2018, Номер 16(11), С. 410 - 410

Опубликована: Окт. 26, 2018

Isolation, finding or discovery of novel anticancer agents is very important for cancer treatment, and seaweeds are one the largest producers chemically active metabolites with valuable cytotoxic properties, therefore can be used as new chemotherapeutic source inspiration to develop ones. Identification more potent selective components isolated from brown, green red seaweeds, well studies their mode action attractive constitute a small but relevant progress pharmacological applications. Several researchers have carried out in vitro vivo various cell lines disclosed among terpenoids, including carotenoids, polyphenols alkaloids that found seaweeds. In this review type antiproliferative effects will discussed additionally action, structure-activity relationship selectivity also revealed. The diterpene dictyolactone, sterol cholest-5-en-3β,7α-diol halogenated monoterpene halomon reported compounds, ones present sub-micromolar cytotoxicity. Additionally, dimeric sesquiterpene cyclolaurane-type, three bromophenols should emphasized because they exhibit half maximal inhibitory concentration (IC50) values between 1–5 µM against several lines.

Язык: Английский

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Electrochemical Oxidative Oxydihalogenation of Alkynes for the Synthesis of α,α-Dihaloketones

Organic Letters, Год журнала: 2020, Номер 22(3), С. 1169 - 1174

Опубликована: Янв. 14, 2020

An electrochemical oxydihalogenation of alkynes has been developed for the first time. Using this sustainable protocol, a variety α,α-dihaloketones can be prepared with readily available CHCl3, CH2Cl2, ClCH2CH2Cl, and CH2Br2 as halogen source under conditions at room temperature.

Язык: Английский

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Nucleophilic Substitution at Quaternary Carbon Stereocenters

Journal of the American Chemical Society, Год журнала: 2020, Номер 142(12), С. 5543 - 5548

Опубликована: Март 6, 2020

Cyclopropyl carbinol derivatives undergo a regio- and stereoselective nucleophilic substitution at the quaternary carbon center, with pure inversion of configuration, to provide acyclic products as single diastereomer. The selectivity is attributed existence cyclobutonium species, reacting most substituted center. Diastereomerically enantiomerically enriched tertiary alkyl bromide, chloride, ester, fluoride could therefore be easily prepared in only three catalystic steps from commercially available alkynes.

Язык: Английский

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Indane-Based Chiral Aryl Chalcogenide Catalysts: Development and Applications in Asymmetric Electrophilic Reactions

Accounts of Chemical Research, Год журнала: 2022, Номер 55(17), С. 2439 - 2453

Опубликована: Авг. 25, 2022

ConspectusAsymmetric electrophilic reactions provide an ideal method for the construction of chiral molecules by incorporating one or more functional groups into parent substrates under mild conditions. However, due to issues reactivities species and possible racemization intermediates as well restriction scaffolds catalysts, many limitations remain in this field, such narrow scopes electrophiles limited types nucleophiles reactions. To overcome synthesis diversified molecules, we developed a series indane-based amino aryl chalcogenide catalysts. These catalysts are easily prepared based on privileged indane scaffold. They can appropriate H-bonding effect varying protecting offer proper Lewis basicity steric hindrance adjusting different substituents motifs. features allow them meet requirements reactivity environment Notably, they have been successfully applied various asymmetric alkenes, alkynes, arenes, expanding field reactions.Using these realized enantioselective CF3S-lactonization olefinic carboxylic acids, CF3S-aminocyclization sulfonamides, desymmetrizing CF3S-carbocyclization gem-diaryl-tethered CF3S-oxycyclization N-allylamides, intermolecular trifluoromethylthiolating difunctionalization allylic C–H trifluoromethylthiolation trisubstituted formally CF3S-oxyfunctionalization aliphatic internal azidothiolation, oxythiolation, thioarylation N-allyl chlorocarbocyclization aryl-tethered diolefins, Friedel–Crafts-type chlorination anilides, dearomatization 1-naphthanilides. Additionally, carbothiolation alkynes construct enantiopure carbon chirality center-containing axially sulfide vinyl arenes aromatic halogenation produce P-chirogenic compounds be accomplished. In reactions, bifunctional binding mode is proposed catalytic cycles, which acid-derived anion-binding interaction might exist account high enantioselectivities reactions.In Account, demonstrate our achievements share thoughts catalyst design, understanding perspectives chalcogenide-catalyzed We hope that experience will promote design development other novel organocatalysts new challenging

Язык: Английский

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