Palladium-Catalyzed Domino Conversion of Aryl–Thianthreniums with Anhydrides: Rapidly Building Highly Functionalized Fluorenones

Organic Letters, Год журнала: 2024, Номер 26(16), С. 3332 - 3337

Опубликована: Апрель 15, 2024

As a class of rising electrophilic coupling reagents, aryl–thianthreniums (aryl-TTs) have been gaining immense attention. Herein, novel palladium-catalyzed domino annulation aryl-TTs with anhydrides is proposed to rapidly assemble collection highly functionalized fluorenones. This finding presents an innovative reaction pattern wherein the version first involved. Heavily compared existing conversions aryl-TTs, this identified process successively functions as four aryl C–H bonds.

Язык: Английский

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Electroreductive Arylcarboxylation of Styrenes with CO₂ and Aryl Halides via a Radical–Polar Crossover Mechanism

Organic Letters, Год журнала: 2024, Номер 26(21), С. 4427 - 4432

Опубликована: Май 17, 2024

2,3-Diaryl propanoic acids are important structures as a result of their widespread presence in numerous bioactive compounds. However, the limitations existing synthetic techniques include requirement for costly catalysts and limited substrates. Here, we developed novel electroreductive arylcarboxylation alkenes with CO2 based on radical–polar crossover pathway assisted by easily accessible dimethyl terephthalate reductive mediator. This method will provide an efficient strategy synthesis 2,3-diarylpropanoic acids.

Язык: Английский

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Visible light-promoted defluorinative alkylation/arylation of α-trifluoromethyl alkenes with thianthrenium salts

Green Chemistry, Год журнала: 2024, Номер 26(17), С. 9371 - 9377

Опубликована: Янв. 1, 2024

Defluorinative alkylation and arylation between thianthrenium salts α-trifluoromethyl alkene to afford gem -difluoroolefins by easily recycling thianthrene under visible light irradiation free of metal photocatalyst.

Язык: Английский

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Palladium-Catalyzed Hiyama-Type Coupling of Thianthrenium and Phenoxathiinium Salts

Organic Letters, Год журнала: 2024, Номер 26(31), С. 6681 - 6686

Опубликована: Июль 26, 2024

Here, we demonstrate palladium-catalyzed Hiyama-type cross-coupling reactions of aryl thianthrenium or phenoxathiinium salts. By employing stable and inexpensive organosilanes, the arylation, alkenylation, alkynylation were realized in high efficiency using commercially available Pd(tBu3P)2 as catalyst, thus providing a reliable method for preparation biaryls, styrenes, acetylenes with broad functional group tolerance under mild conditions. Given accessibility salts from simple arenes remarkable regioselective fashion, this protocol also provides an attractive approach late-stage modification complex bioactive scaffolds.

Язык: Английский

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Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8821 - 8826

Опубликована: Окт. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Язык: Английский

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Mechanochemically Induced Thianthrenium Salts-Based Arylation of Diverse Heterocyclic Scaffolds

ACS Sustainable Chemistry & Engineering, Год журнала: 2024, Номер 12(34), С. 12808 - 12818

Опубликована: Авг. 15, 2024

Herein, a mechanochemically triggered C–H arylation of coumarins, quinoline-N-oxides, and uracil molecules with aryl thianthrenium salts is described. Aryl are primarily acknowledged for their expedient reusability adherence to atom economy principles. Mechanistic studies suggested that mechanical stress promoted the homolytic scission C–S bond salts, forming radical intermediate. Later, intermediate engaged in addition reaction above heterocycles, leading desired products good yields. This versatile protocol accommodates wide range functional groups facilitates synthesis bioactive compounds drug molecules.

Язык: Английский

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Alkene Carboxy-Alkylation via CO₂^•–

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(51), С. 35035 - 35042

Опубликована: Дек. 12, 2024

Herein, we introduce a new platform for alkene carboxy-alkylation. This reaction is designed around CO

Язык: Английский

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Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Июнь 3, 2024

A dearomative oxidation of pyrroles to Δ

Язык: Английский

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Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives

Advanced Science, Год журнала: 2024, Номер 12(2)

Опубликована: Ноя. 21, 2024

Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular streamlined synthesis of a diverse library peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, visible light‐induced three‐component reaction involving arylthianthrenium salts, acid/peptide derivatives, alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex molecules. method offers promising alternative route for peptide‐derived bio‐relevant compounds

Язык: Английский

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Photoredox-catalyzed synthesis of α,α-difluoromethyl-β-alkoxysulfones from sulfur dioxide

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 109926 - 109926

Опубликована: Апрель 1, 2024

Язык: Английский

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