Modifications of Terpenoids via Inert Aliphatic C−H Bonds Heteroarylation with Heteroarenes

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A method to modify commercially available terpenoids via inert aliphatic C–H bond heteroarylation directly with heteroarenes catalyzed by decatungstate anion is developed.

Язык: Английский

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Tandem dehydrogenation-olefination-decarboxylation of cycloalkyl carboxylic acids via multifold C–H activation

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Июнь 25, 2024

Abstract Dehydrogenation chemistry has long been established as a fundamental aspect of organic synthesis, commonly encountered in carbonyl compounds. Transition metal catalysis revolutionized it, with strategies like transfer-dehydrogenation, single electron transfer and C–H activation. These approaches, extended to multiple dehydrogenations, can lead aromatization. Dehydrogenative transformations aliphatic carboxylic acids pose challenges, yet engineered ligands initiate dehydrogenation via activation, though outcomes vary based on substrate structures. Herein, we have developed catalytic system enabling cyclohexane undergo multifold activation furnish olefinated arenes, bypassing lactone formation. This showcases unique reactivity acids, involving tandem dehydrogenation-olefination-decarboxylation-aromatization sequences, validated by control experiments key intermediate isolation. For cyclopentane reluctant aromatization, the facilitates controlled dehydrogenation, providing difunctionalized cyclopentenes through dehydrogenation-olefination-decarboxylation-allylic acyloxylation sequences. transformation expands into diverse molecular entities wide applications, underscoring its importance.

Язык: Английский

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Synthesis of chiral carbocycles via enantioselective β,γ-dehydrogenation

Nature Synthesis, Год журнала: 2024, Номер 3(12), С. 1550 - 1559

Опубликована: Авг. 15, 2024

Язык: Английский

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Direct synthesis of alkylated 4-hydroxycoumarin derivatives via a cascade Cu-catalyzed dehydrogenation/conjugate addition sequence

Chemical Communications, Год журнала: 2023, Номер 59(44), С. 6686 - 6689

Опубликована: Янв. 1, 2023

An efficient approach for the direct synthesis of alkylated 4-hydroxycoumarin derivatives via a Cu-catalyzed cascade dehydrogenation/conjugate addition sequence starting from simple saturated ketones and 4-hydroxycoumarins has been developed. This protocol features excellent functional-group tolerance, easy scale-up, broad substrate scope including bioactive molecules. More importantly, series marketed drugs, such as warfarin, acenocoumarol, coumachlor, coumafuryl, can be obtained by this method.

Язык: Английский

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The Role of Ligands and Silver(I) Additives in the Ligand-Promoted Divergent α,β-Dehydrogenation of Aliphatic Acids

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 14263 - 14273

Опубликована: Сен. 12, 2024

Язык: Английский

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