Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Год журнала: 2024, Номер 35(11), С. 109683 - 109683

Опубликована: Март 2, 2024

Язык: Английский

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Selective synthesis of pyridazin-fused chromones and 3-pyridazinyl chromones through intermolecular chromone annulation of o-hydroxyphenylenaminones with aryldiazonium salts

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3906 - 3912

Опубликована: Янв. 1, 2024

A chemodivergent and skeleton-controllable annulation reactions of readily available o -HPEs aryldiazonium salts was described for the synthesis highly functionalized pyridazine-fused chromones with high antiviral activity higher safety.

Язык: Английский

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Divergent Synthesis of 2-Chromonyl-3-hydrazono-chromones and 2-Alkoxy-3-hydrazono-chromones through Switchable Annulation Reactions of o-Hydroxyphenylenaminones with Aryldiazonium Salts

Organic Letters, Год журнала: 2024, Номер 26(23), С. 4980 - 4985

Опубликована: Июнь 4, 2024

An unprecedented selective chromone annulation reaction controlled by solvent for the divergent synthesis of two types 2,3-disubstituted skeletons has been developed. A variety 2-chromonyl-3-hydrazono-chromones and 2-alkoxy-3-hydrazono-chromones were constructed efficiently from readily available

Язык: Английский

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Progress Toward Sustainable Polymer Technologies with Ball-Mill Grinding

Progress in Polymer Science, Год журнала: 2024, Номер unknown, С. 101900 - 101900

Опубликована: Окт. 1, 2024

Язык: Английский

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Mechanochemical Synthesis of Trifluoromethyl Arenes: Nanocellulose-Supported Deaminative Trifluoromethylation of Aromatic Amines

ACS Sustainable Chemistry & Engineering, Год журнала: 2024, Номер 12(24), С. 8980 - 8989

Опубликована: Июнь 6, 2024

A convenient one-pot procedure for the mechanochemical nanocellulose-supported synthesis of trifluoromethyl arenes has been developed through selective transformation an aromatic amino group into functionality using pyrylium tetrafluoroborate (Pyry-BF4) and trifluoromethyltrimethylsilane (TMSCF3) via in situ formation pyridinium salt intermediate under transition metal-free conditions. The nanocellulose acts here as a green reaction medium, does not occur without this additive. scope present protocol includes 28 excellent yields (ipso-)substitution (SNAr) with CF3 functionality. This method could have great significance pharmaceutical industries late-stage functionalization active ingredients (APIs)/drugs.

Язык: Английский

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Nanocellulose as Reaction Medium for FeCl₃‐Mediated Mechanochemical Deaminative Fluorination of (Hetero)aromatic Amines

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Июнь 3, 2024

Abstract The development of an efficient alternative to the widely employed Balz‐Schiemann deaminative fluorination method (i. e. without using aryl diazonium tetrafluoroborate salt) is a challenging task. Herein, we report convenient one‐pot for FeCl 3 ‐nanocellullose mediated mechanochemical synthesis fluoroarenes through selective substitution aromatic amino group by fluorine pyrylium (Pyry‐BF 4 ) and sodium fluoride (NaF) via in situ formation pyridinium salt intermediate. scope present protocol includes thirty‐four organofluorine compounds with excellent yields (S N Ar) fluorine. presented concise methodology opens pathway access new chemical spaces late‐stage functionalization pharmaceutical industries.

Язык: Английский

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Nanocellulose as a Reaction Media and Stoichiometric Reagent for FeCl₃-Mediated Reductive Functionalization of Nitro Compounds

ACS Sustainable Chemistry & Engineering, Год журнала: 2023, Номер 12(1), С. 1 - 9

Опубликована: Дек. 19, 2023

Among a wide array of synthetic amides, N-aryl/alkyl amides are an important class structural motifs having significant importance in pharmaceutical and agrochemical industries. In this regard, rapid, low-cost, environmentally friendly synthesis still remains high demand. Herein, we report convenient route for the mechanochemical via FeCl3-catalyzed reductive amidation nitro compounds, as well acylation aliphatic/aromatic amines with carboxylic acids using nanocellulose reaction media/stoichiometric reducing agent. The protocol was found to be simple, efficient, benign obtain diverse respective good excellent yields. Furthermore, use amines, cheap readily available starting materials, FeCl3 nontoxic catalyst, biodegradable media stoichiometric agent makes category green chemical transformation.

Язык: Английский

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Eco-Friendly and Efficient Synthesis of 2-Hydroxy-3-Hydrazono-Chromones Through α,β-C(sp2)–H Bond Difunctionalization/Chromone Annulation Reaction of o-Hydroxyaryl Enaminones, Water, and Aryldiazonium Salts

Molecules, Год журнала: 2025, Номер 30(6), С. 1194 - 1194

Опубликована: Март 7, 2025

A novel, eco-friendly, and efficient method for constructing 2,3-disubstituted chromone skeletons from readily available water, o-hydroxyaryl enaminones (o-HPEs), aryldiazonium salts has been developed under mild reaction conditions. This α,β-C(sp2)–H bond difunctionalization/chromone annulation strategy is achieved by building two C(sp3)–O bonds a C(sp2)-N bond, which provides practical pathway the preparation of 2-hydroxy-3-hydrazono-chromones in moderate to excellent yields, enabling broad substrate scope good functional group tolerance, as well gram-scale synthesis. protocol offers valuable tool synthesizing diverse functionalized chromones with potential applications drug discovery industrial

Язык: Английский

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Ruthenium Catalyzed Mechanochemical Transformation of Sulfonamide Group to Fluoro, Trifluoromethyl, and Trifluoromethoxy Functionalities

Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown

Опубликована: Апрель 9, 2025

Abstract A convenient route for the mechanochemical synthesis of fluorinated aromatic compounds, that is, fluoro, trifluoromethyl, and trifluoromethoxy arenes, has been developed via pyrylium tetrafluoroborate (Pyry‐BF 4 )‐mediated desulfonamidative cross‐coupling primary sulfonamides under synergy a piezoelectric material BaTiO 3 , Ru‐catalysis. This is first‐ever report on selective transformation sulfonamide (SO 2 NH ) functionality to CF /OCF /F group in single step ball‐milling conditions. Considering importance as valuable pharmacophores, present approach could have potential get synthetic utility pharmaceutical industries late‐stage functionalization drugs related active ingredients (APIs).

Язык: Английский

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Mechanochemical Sequential Deoxygenative Cross-Coupling Reactions of Phenols Under Ruthenium-Nickel Catalysis

Molecules, Год журнала: 2025, Номер 30(8), С. 1835 - 1835

Опубликована: Апрель 19, 2025

Herein, we report the first mechanochemical strategy for Ru-catalyzed deoxygenative borylation of free phenols via C-O bond cleavage. This phenolic approach has been successfully extended to Suzuki-Miyaura-type cross-coupling with aryl bromides. The protocol accepts a wide scope substrates, allowing synthesis pinacolboranes and biphenyl structures in excellent yields serving as better alternative classical reactions context pot, atom, step economy synthesis.

Язык: Английский

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