Light-induced arylation (alkylation) of N-sulfonylhydrazones with boronic acids

Chemical Communications, Год журнала: 2024, Номер 60(20), С. 2796 - 2799

Опубликована: Янв. 1, 2024

We report light-induced arylation (alkylation) for the synthesis of diarylmethanes, bis(diarylmethyl)benzenes, arylalkylmethanes, and triarylmethanes from readily accessible N -sulfonylhydrazones aryl/alkylboronic acids with aid Cs 2 CO 3 .

Язык: Английский

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Electrophilic Halogenation of Allenoates and 3-Alkynoates: Synthesis of 1,4-Dicarbonyl (E)-3-Haloalkenes and Mechanistic Investigations

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

Опубликована: Март 26, 2025

Allenoates traditionally provide halobutenolides upon reaction with halonium ions via electrophile-assisted halolactonization. Herein, an unusual electrophilic halogenation of di- and trisubstituted allenoates 3-alkynoates is demonstrated N-halosuccinimides under DABCO promotion. The protocol affords densely functionalized 1,4-dicarbonyl 3-haloalkenes in good yields excellent (E)-stereoselectivity (up to 83% yield, >20:1 dr). are presumed form γ-haloallenoate intermediates, which further react the desired scaffolds. role nucleophilic base transformation demystified through control experiments computational studies. deliverables identified as synthons for various synthetic group transformations valuable targets biologically active pyridazine

Язык: Английский

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Facile Access to Hindered Ethers via Photoinduced O–H Bond Insertions

ACS Central Science, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

Язык: Английский

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Photoactivation of Hydrazones for the Synthesis of Diarylalkanes and Trialkylmethylboronates: The Key Role Played by Soluble Base

Organic Letters, Год журнала: 2024, Номер 26(16), С. 3397 - 3400

Опубликована: Апрель 11, 2024

The synthesis of diaryl alkanes and tertiary organoboronates via Barluenga coupling at room temperature occurred photoactivated conversion aryl sulfonyl hydrazones to diazo compounds in the presence soluble bases. combination arylsulfonyl hydrazone a base is necessary provide near-UV chromophore. Using aromatic boronic acids resulted rapid deboronation because instability dibenzylic boron intermediates. Alkyl allowed isolation derivatives boronate.

Язык: Английский

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Catalyst-free photoinduced C(sp3)-C(sp3) bond formation through C-H insertions using non-activated alkanes/ethers

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 14, 2024

Язык: Английский

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Deoxygenative Geminal Silylboration of Amides Using Silylboronates: Synthesis and Use of α-Boryl-α-Silylalkylamines

Опубликована: Май 22, 2024

α-Silylalkylamines and a-borylalkylamines are versatile synthetic intermediates attractive scaffolds found in pharmaceutical drugs agrochemicals. Despite great progress on methods for preparation of α-silylalkylamines or a- borylalkylamines, there no general strategies α- boryl-α-silylalkylamines the reactivity has not been explored. Here we report deoxygenative geminal silylboration amides using silylboronates presence alkoxide base catalyst, producing boryl-a-silylalkylamines. The silicon boron groups α-boryl-α-silylalkylamines to be utilized chemoselective transformations, such as protonation alkylation. This protocol serves various α-borylalkylamines from readily available amides.

Язык: Английский

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Synthesis of Secondary Boronates via Deaminative Cross‐Coupling of Alkyl Nitroso Carbamates and Boronic Acids

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(37)

Опубликована: Авг. 2, 2024

Abstract A strategy for transition metal‐free cross‐coupling of alkyl nitroso‐carbamates and boronic acids is reported. The N ‐nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows synthesis a wide variety secondary boronates, benzylic boronates formal Csp 3 −Csp 2 products under operationally conditions. Functional group tolerance also demonstrated applied modification lysine to make non‐canonical amino acids.

Язык: Английский

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Acetone Serving as a Solvent and Interaction Partner Promotes the Direct Olefination of N-Tosylhydrazones under Visible Light

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6180 - 6192

Опубликована: Апрель 18, 2024

The photochemistry of noncovalent interactions to promote organic transformations is an emerging approach providing fresh opportunities in synthetic chemistry. Generally, the external substance necessary add as interaction partner, thereby sacrificing atom economy reaction. Herein, we describe a catalyst-free and interaction-mediated strategy access olefination N-tosylhydrazones using acetone solvent partner. This protocol also features broad substrate scope, excellent functional group compatibility, mild reaction conditions without transition metals. Moreover, gram-scale synthesis olefins generation pharmaceutical intermediates highlighted its practical applicability. Lastly, mechanistic studies indicate that was initiated via between N-tosylhydrazone anion, which supported by density theory calculations.

Язык: Английский

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N–H Insertion of Anilines on N-Tosylhydrazones Induced by Visible Light Irradiation

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11620 - 11630

Опубликована: Июль 26, 2024

Diazo compounds and their precursors represent an interesting chemical category for organic synthesis. Particularly, N-tosylhydrazones have attracted attention easy accessibility diverse reactivity, including carbene transfer reactions. We described a visible light-induced N–H insertion reaction of anilines on in situ-generated diazo compounds. Optimal conditions using DBU toluene efficiently yielded the desired products. Mechanistic studies enabled us to trap intermediate that plays key role transformation.

Язык: Английский

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Synthesis of Secondary Boronates via Deaminative Cross‐Coupling of Alkyl Nitroso Carbamates and Boronic Acids

Angewandte Chemie, Год журнала: 2024, Номер 136(37)

Опубликована: Авг. 2, 2024

Abstract A strategy for transition metal‐free cross‐coupling of alkyl nitroso‐carbamates and boronic acids is reported. The N ‐nitroso carbamates are easily prepared from the corresponding amine in two simple steps. This method allows synthesis a wide variety secondary boronates, benzylic boronates formal Csp 3 −Csp 2 products under operationally conditions. Functional group tolerance also demonstrated applied modification lysine to make non‐canonical amino acids.

Язык: Английский

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