Palladium(ii)-catalyzed intramolecular C–H amination to carbazole: the crucial role of cyclic diacyl peroxides

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(16), С. 4529 - 4538

Опубликована: Янв. 1, 2024

Herein, we have developed an efficient Pd II -catalyzed intramolecular oxidative C–H amination under additive-free and green conditions where strained cyclic diacyl peroxide functions as both a sacrificial oxidant bidentate linker.

Язык: Английский

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Enabling Site-Selective C–H Functionalization of Aliphatic Alcohols and Amines with exo-Directing Groups by Tether-Tunable Design of Pd^II/Pd^IV Catalysis

ACS Catalysis, Год журнала: 2024, Номер 14(22), С. 17077 - 17083

Опубликована: Ноя. 5, 2024

We report herein a general platform for palladium catalysis using library of cyclic diacyl peroxides, achieving site-selective C–H functionalization aliphatic alcohols and amines. Experimental studies theoretical calculations indicate that bystanding peroxides minimize unwanted reductive elimination events enable controlled cleavage. The protocol is simple scalable offers high selectivity broad range substrates nucleophiles, including complex molecules. findings advance understanding high-valent chemistry, providing tool creating chemically diverse vicinal diols amino opening new possibilities in functionalization.

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 Generation and Cycloadditions of Strained Cycloalkynes

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

Опубликована: Апрель 20, 2025

Strained cycloalkynes and their utilization have enabled prospective tactical strategies for synthetic medicinal chemistry, chemical biology, materials science, allied fields. However, full potential remains largely underexplored due to the limited availability of efficient sp3-rich cycloalkyne precursors with high efficiency structural complexity. Herein, we describe an intuitive modular photochemical approach liberate analogs from cyclic diacyl peroxides, without external reagents. This disclosed platform hinges on leverage realize two distinct classes strain-promoted cycloadditions straightforward construction diverse polycyclic scaffolds production any side product except nitrogen CO2. Moreover, functional group tolerance, biorelevant molecules compatibility, scalability, late-stage functionalization bioactive demonstrate utility presented methods. These features enrich assembling cycloalkenyl-containing diversity, offering new opportunities click chemistry bioorthogonal reactions.

Язык: Английский

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Photoinduced cross-coupling of aryl halides enabled by n-tetrabutylphosphonium phthalate

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(23), С. 6718 - 6727

Опубликована: Янв. 1, 2024

Phthalate acts as an electron shuttle bridge to realize aryl cross-coupling reactions by two-point non-covalent interaction.

Язык: Английский

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Stereocontrolled and time-honored access to piperidine- and pyrrolidine-fused 3-methylenetetrahydropyrans using lactam-tethered alkenols

RSC Advances, Год журнала: 2024, Номер 14(37), С. 26913 - 26919

Опубликована: Янв. 1, 2024

Two cascade approaches featuring bromocycloetherification-elimination or dehydrogenative cycloetherification-isomerization of lactam-tethered alkenols have facilitated the stereocontrolled synthesis lactam-fused 3-methylenetetrahydropyrans.

Язык: Английский

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