A variable bidentate traceless directing group for nickel-catalyzed regioselective B–H poly-chalcogenation of o-carboranes

Inorganic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A nickel-catalyzed direct cage B–H poly-chalcogenation of icosahedral carborane clusters, enabled by a variable bidentate 8-aminoquinoline traceless directing group, has been developed under oxidant-free and weakly basic conditions.

Language: Английский

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Palladium-Catalyzed Cross-Coupling Reactions of Carboranes with Alkenes via Selective B–H Bond Activation

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

A palladium-catalyzed Heck-type cross-coupling reaction of carboranes with alkenes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was realized. This shows good B(9) selectivity for m-carboranes and is also suitable o- p-carborane. Meanwhile, a series mono-, di-, trisubstituted were compatible substrates to afford the alkenylated products 16–89% yields. The 1,2-bis(carboranyl)ethylene first synthesized by vinyltrimethylsilane m-carborane. Further transformations C═C bond product examined hydroboration oxidation, hydroboration, bromination generate corresponding B(9)-functionalized m-carboranes.

Language: Английский

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Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Organoselenium compounds and quinolines are widely used in drugs materials. Herein, we report an electro-oxidative cyclization between isocyanides diselenides to effectively synthesize 2-organoselenyl a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series produced with up 82% yield, good functional group tolerance high atom efficiency under room temperature.

Language: Английский

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A Pd-catalyzed route to carborane-fused boron heterocycles

Chemical Science, Journal Year: 2024, Volume and Issue: 15(27), P. 10392 - 10401

Published: Jan. 1, 2024

A Pd-catalyzed cross-coupling system has been developed to achieve vicinal diamination of 9,10-dibromo-carborane with NH-heterocycles and anilines. These products can be further converted carborane-fused six- seven-membered heterocycles.

Language: Английский

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Palladium‐Catalyzed Direct B—H Oxygenation: Facile Synthesis of o‐Carboranofuranones^†

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(23), P. 3083 - 3087

Published: Aug. 8, 2024

Comprehensive Summary Recent advances in transition metal‐catalyzed o ‐carborane B—H activation have led to the rapid development of various methodologies for cage boron functionalization. For catalytic acyloxylation, intermolecular oxygenation gave products with different regioselectivities (B(3)‐, B(4)‐, and B(8,9)‐selectivities). Herein, an efficient palladium‐catalyzed direct B(4)–H ‐carboranylacetic acids has been achieved, where carboxylic group serves as not only a directing group, but also coupling partner. A wide range substituted cyclized via formation B(4)−O bond give corresponding γ‐lactones modest excellent yields. Pd(IV) intermediate is proposed be involved cycle. This work offers valuable references BH/OH dehydrocoupling reactions under mild conditions produce carborane‐featuring functional molecules.

Language: Английский

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Pd-Catalysed synthesis of carborane sulfides from carborane thiols

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Carboranes are an interesting class of aromatic molecules with icosahedral geometry, high stability, and unique electronic effects.

Language: Английский

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Recent Advances in Visible Light Photocatalytic and Transition Metal-Catalyzed Synthesis of Disulfide Compounds

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Reviewing photocatalytic and metal-catalyzed disulfide synthesis, 2021–2024, emphasizes efficiency, selectivity, sustainability for drug material science.

Language: Английский

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