Flavin-Mediated Photocatalysis Provides a General Platform for Sulfide C–H Functionalization

ACS Catalysis, Год журнала: 2024, Номер 14(4), С. 2395 - 2401

Опубликована: Янв. 31, 2024

Functionalized sulfides are important in many areas of science, ranging from chemical biology through drug discovery to organic materials chemistry. Sulfides bearing pendant reactive groups the α-position particularly useful; however, methods for selective valorization simple or late-stage functionalization complex by convenient addition valuable functionality underexplored. Here we exemplify a general reaction platform sulfide showcasing three modes α-sulfur C-H functionalization; cyanation, alkenylation, and alkynylation. Using inexpensive commercially available riboflavin tetraacetate visible light, decoration both feedstock proceeds good yield with high selectivity. Methionine-containing peptides can also be selectively functionalized tolerance screen using amino-acid dopants suggests that is compatible most side chains thus potential tool bioconjugation.

Язык: Английский

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Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4972 - 5027

Опубликована: Янв. 1, 2023

This review comprehensively summarizes the dichalcogenative functionalization of unsaturated compounds over past decade. The scopes, limitations and detailed reaction mechanisms are also discussed.

Язык: Английский

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Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis

Molecules, Год журнала: 2022, Номер 27(19), С. 6583 - 6583

Опубликована: Окт. 4, 2022

The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As result, the field of atropisomer synthesis attracted considerable interest within chemistry communities. To date, range catalytic atroposelective approaches reported efficient construction these challenging scaffolds. However, greatly concise highly useful methodologies compounds, focusing on transition-metal, amine, phosphoric acid catalysis reactions, etc., are still desirable. Hence, it is indispensable to succinctly systematically present all such reports means disclosing mechanistic analysis application, as well challenges issues associated establishment atropisomers. In this review, we summarize development asymmetric synthetic strategies access non-biaryl atropisomers rotating around axis, including reaction methods, mechanism, late-stage transformations, applications.

Язык: Английский

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Electrocatalytic Multicomponent Cascade Cross‐Coupling for the Synthesis of Chalcogenosulfonates

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(17), С. 2049 - 2055

Опубликована: Май 7, 2024

Comprehensive Summary An electrocatalytic multicomponent cascade cross‐coupling for the synthesis of chalcogenosulfonates has been established. This approach does not require use transition metals, acids, and external oxidants. The gentle conditions tolerance to a wide variety functional groups permit derivatization complex indoles.

Язык: Английский

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Photocatalyzed Thiosulfonylation of Sila-enynes with Thiosulfonates

Organic Letters, Год журнала: 2023, Номер 25(16), С. 2846 - 2851

Опубликована: Апрель 14, 2023

A photocatalyzed coupling-cyclization of sila-enynes with thiosulfonates has been developed. This reaction provides an efficient strategy to assemble thiosulfone-bifunctionalized benzosilacycles via sequential radical addition and coupling.

Язык: Английский

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S-(Methyl-d₃) Arylsulfonothioates: A Family of Robust, Shelf-Stable, and Easily Scalable Reagents for Direct Trideuteromethylthiolation

Organic Letters, Год журнала: 2022, Номер 24(37), С. 6794 - 6799

Опубликована: Сен. 14, 2022

A family of electrophilic deuterated methylthiolating reagents, S-(methyl-d3) arylsulfonothioates, was developed in two or three steps from cheap d4-MeOH high yields. S-(Methyl-d3) arylsulfonothioates represent a kind powerful reagent and allow modular trideuteromethylthiolation with variety nucleophiles electrophiles including aryl(hetero) iodides, boronic acids esters, terminal alkynes, diazonium salts, β-ketoester, oxindole under mild reaction conditions. structure–reactivity research (SAR) study conducted provided new avenue for the development reagents efficient methodology trideuteromethylthiolation.

Язык: Английский

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Divergent Trideuteromethylthiolation and Aminotrideuteromethylthiolation of Alkenes with N-Fluorobenzenesulfonimide and CD₃SSO₃Na

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7078 - 7082

Опубликована: Сен. 21, 2023

A metal-free oxidative trideuteromethylthiolation of alkenes with CD3SSO3Na using NFSI as an oxidant has been developed. The aminotrideuteromethylthiolation a three-component reaction could be easily achieved in the presence cobalt catalyst. divergent alkenes, readily available reagent, and versatile synthetic strategy allow for late-stage modification drug molecules.

Язык: Английский

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Four-Component Radical 1,2-Selenosulfonylation of Allenes

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5705 - 5712

Опубликована: Июнь 27, 2024

Selenosulfones, as pivotal pharmaceutical molecule frameworks, have become a research hotspot in modern organic synthesis due to their vital need for efficient preparation. Herein, we developed an iron-catalyzed four-component controllable radical tandem reaction of allenes involving cycloketone oxime esters, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), and diphenyl diselenides the complex selenosulfones. This is first case achieving 1,2-selenosulfonylation via process, wherein precise control rates polarity matching enhance high regioselective conversion. The conditions are ecofriendly mild with step-efficiency by forming two new C–S bonds one C–Se bond pot. Moreover, can be achieved replacing esters aryldiazonium tetrafluoroborates this system.

Язык: Английский

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Metal-free three-component amino- and carbotrideuteromethylthiolation of alkenes in water

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(21), С. 6064 - 6068

Опубликована: Янв. 1, 2024

Three-component amino- and carbotrideuteromethylthiolation of alkenes in water.

Язык: Английский

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Straightforward Access to 4-Sulfenylated Isocoumarins via Sulfoxides/MOMCl-Enabled Regioselective Cleavage and Reconfiguration of C–S Bonds

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

The combination of sulfoxides with MOMCl has been found for the first time to mediate electrophilic cyclization and install a variety sulfenyl groups onto isocoumarin skeletons via regioselective cleavage reconfiguration C-S bonds. Notably, MOMCl, mild readily available alkyl chloride, was indispensable played significant role as an activator under neutral conditions in this transformation, thus expanding scope acid-labile substrates.

Язык: Английский

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