Recent advances in organocatalytic enantioselective syntheses of β-fluoroamine compounds

Molecular Catalysis, Год журнала: 2025, Номер 576, С. 114944 - 114944

Опубликована: Фев. 26, 2025

Язык: Английский

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Meta-, Regioselective Amination of Cyclic Diaryliodoniums through C–I and C–O Bond Cleavages: An Access to Functionalized Coumarins

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

Опубликована: Фев. 26, 2025

Despite the widespread ortho-functionalization of cyclic diaryliodoniums in organic chemistry, corresponding meta-functionalization is less explored. Herein, we report a practical meta-selective activation hypervalent iodoniums for synthesis 4-amino coumarin derivatives broad functional group tolerance and environmentally friendly manner. The practicability this protocol was further highlighted by late-stage modification some common pharmaceuticals natural products.

Язык: Английский

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Synthesis of N-Heterocycle-Ligated Porphyrins Using Iodobenzene Diacetate Enabled Regioselective Cross-Dehydrogenation of Porphyrins and NH-Heteroaromatics

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

Опубликована: Март 2, 2025

Preparation of diverse meso-functionalized porphyrins involves iodine(III)- and copper triflate-promoted dehydrogenative coupling meso-free appropriate NH-free heterocycles. Reaction conditions involving the stable recyclable iodobenzene diacetate reagent are compatible with a range heterocycles (acridone, phenoxazine phenothiazine, carbazole, β-carbolin triazoles, imidazole, pyrazole, indazole, tetrazole) to access diversely functionalized A3B, A2BC, A2B2 in moderate good yields. The prepared heterocycle-appended exhibit modestly red-shifted Soret Q bands absorption spectra.

Язык: Английский

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Elucidation of the Active Mn-Species Responsible for Alkane Fluorination Catalyzed by Mn Porphyrins

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4499 - 4506

Опубликована: Март 2, 2025

Язык: Английский

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Sustainable and scalable one-pot synthesis of diaryliodonium salts

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Two one-pot syntheses of diaryliodonium triflates are presented, rendering the production these electrophilic arylating agents more sustainable.

Язык: Английский

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Catalytic Fluorination of α-Branched Ketones with Nucleophilic Fluorine

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 24, 2025

We herein disclose the first example of metal-free, redox-umpolung-enabled catalytic fluorination α-branched ketones with nucleophilic fluorine by judicious choice an oxidant. The strategic use cyclopropyl malonoyl peroxide in hypervalent iodine(III) catalysis expands modularity and generality construction α-fluorinated ideally orthogonal reactivity space, avoiding competing oxidation processes. Characteristic for this transformation is its operational simplicity, mild reaction conditions, gram-scale synthetic ability.

Язык: Английский

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Photochemical Dual Radical Coupling of Carboxylates with Alkenes/Heteroarenes via Diradical Equivalents

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Март 24, 2025

Carboxylate diradical intermediates, with α-carbon and carboxylic oxygen acting as reactive radical centers, represent a highly attractive long-sought species in reaction design synthesis. However, capturing these intermediates for coupling reactions poses formidable challenge due to their inherent instability spontaneous decarboxylation. Here, we addressed this by temporarily masking the carboxylate reactivity via photocleavable dynamic oxygen–iodine bond. This approach effectively prevents unwanted decarboxylation enables controlled utilization of forming new bonds. Carboxylates alkenes/heteroarenes, among most readily available raw materials, can now seamlessly couple pathways form γ-butyrolactones, which are common motifs found numerous natural products bioactive molecules. Ionic traditional carboxylates ruled out based on experimental studies density functional theory (DFT) calculations. strategy overcomes substrate limitations methods, significantly expanding range applicable alkenes/heteroarenes. Our method allows transforming alkenes modes diverse offers insights into developing di- multiradical equivalents unprecedented synthetic designs.

Язык: Английский

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Multisubstituted Indoles by a Dual Gold/Silver-Catalyzed Aminoalkynylation of 2-Alkynylanilines

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 30, 2025

A straightforward and efficient method for the synthesis of multisubstituted indoles has been developed through a dual gold/silver-catalyzed aminoalkynylation 2-alkynylanilines using hypervalent iodine(III) reagents under open-air conditions. This approach features in situ generation alkynyl Au(III) species, which facilitates with excellent functional group tolerance high yields. Mechanistic studies reveal that gold(III) intermediate plays crucial role reaction pathway. Moreover, protocol is scalable to gram quantities offers potential further transformation into diverse functionalized compounds.

Язык: Английский

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Diazomethyl-λ³-iodane meets aryne: Dipolar cycloaddition and C-to-N iodane shift leading to indazolyl-λ³-iodanes

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Diazomethyl-λ 3 -iodanes have recently emerged as carbyne equivalents in organic synthesis, enabling the construction of multi-substituted carbon centers through strategic sequential activation diazo and iodane functional groups. Distinct from...

Язык: Английский

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Benzothiazolines Acting as Carbanion and Radical Transfer Reagents in Carbon–Carbon Bond Construction

Molecules, Год журнала: 2025, Номер 30(8), С. 1711 - 1711

Опубликована: Апрель 11, 2025

Traditionally employed as hydrogenation reagents, benzothiazolines have emerged versatile carbanion and radical transfer playing a vital role in the construction of various carbon–carbon bonds. The cutting-edge progress photochemistry chemistry prompted study visible light-driven reactions, bringing into vibrant focus. Their chemical processes been uncovered to encompass variety activation mechanisms, with five distinct modes having identified. This work reviews innovative applications donors alkyl or acyl groups, achieving hydroalkylation hydroacylation substitution. By examining their diverse this review highlights potential serving groups for further research development. Moreover, will offer exemplary inspiration synthetic chemists, contributing ongoing evolution utility organic synthesis.

Язык: Английский

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