Late-Stage C–H Nitration of Unactivated Arenes by Fe(NO₃)₃·9H₂O in Hexafluoroisopropanol

Organic Letters, Год журнала: 2024, Номер 26(15), С. 3316 - 3320

Опубликована: Апрель 10, 2024

Operationally simple and generally applicable arene nitration with cheap easily accessible chemicals has been a long-sought transformation in the synthetic organic community. In this work, we realized goal nontoxic inexpensive Fe(NO3)3·9H2O as nitro source recyclable solvent hexafluoroisopropanol promotor via network of hydrogen-bonding interactions. As result relative mildness high reliability protocol, late-stage various highly functionalized natural products commercially available drugs was realized.

Язык: Английский

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Selective Arene Photonitration via Iron-Complex β-Homolysis

JACS Au, Год журнала: 2024, Номер 4(12), С. 4899 - 4909

Опубликована: Ноя. 21, 2024

Nitroaromatics, as an important member and source of nitrogen-containing aromatics, is bringing enormous economic benefits in fields pharmaceuticals, dyes, pesticides, functional materials, fertilizers, explosives. Nonetheless, the notoriously polluting nitration industry, which suffers from excessive discharge fumes waste acids, poor group tolerance, tremendous purification difficulty, renders mild, efficient, environmentally friendly a formidable challenge. Herein, we develop visible-light-driven biocompatible arene C–H strategy with good efficiency regioselectivity, marvelous substrate applicability wide application scale-up synthesis, total late-stage functionalization. A nitryl radical delivered through unusual β-homolysis photoexcited ferric-nitrate complex proposed to be key nitrification reagent this system.

Язык: Английский

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Electrophilic (Hetero)Arene C–H Nitration by Ferric Nitrate Nonahydrate in Hexafluoroisopropanol

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

Опубликована: Май 15, 2025

In this article, we provide an extended substrate scope and more detailed mechanistic studies of operationally simple generally applicable arene nitration that previously reported. This method utilizes safe inexpensive Fe(NO3)3•9H2O as the nitro source in easily recyclable HFIP obviates need for corrosive acids (HNO3 + H2SO4). As a result, speculated it could serve effective substitute traditional mixed acid approach under most scenarios due to its operational simplicity. A general guidance application was provided.

Язык: Английский

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Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 9816 - 9829

Опубликована: Июнь 25, 2024

Various substituted pyrrolo[1,2-

Язык: Английский

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Bio-Inspired Consecutive Photocatalyzed C–H Nitration of Arenes

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

Опубликована: Март 19, 2025

Concerned with traditional nitration methods requiring high temperatures, strong acids, or oxidizing agents, we developed an acid-free, selective photocatalytic method using riboflavin tetraacetate and Fe(NO3)3·9H2O under visible light. This efficiently nitrates various arenes bioactive molecules selectivity functional group tolerance, offering a sustainable alternative to techniques.

Язык: Английский

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Synthesis of Furan-Containing Pyrrolo[2,1-a]Isoquinoline Derivatives Based on Phosphoranylidenesucciminide

Chemistry of Natural Compounds, Год журнала: 2025, Номер unknown

Опубликована: Март 26, 2025

Язык: Английский

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Site-Selective Nitration of Arene via Hypervalent Iodine-Mediated C–H Functionalization

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 7, 2025

We developed a novel nitration method using hypervalent iodine for site-selective C-H functionalization. This technique efficiently synthesizes nitroarenes with high regioselectivity and is scalable, enhancing the late-stage modification of bioactive pharmaceuticals.

Язык: Английский

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Nitration of Pyrrolo[2,1‐a]isoquinolines with NaNO₂/HFIP

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(16)

Опубликована: Фев. 23, 2024

Abstract A mild nitration of pyrrolo[2,1‐ a ]isoquinolines has been reached using sodium nitrite as nitro source in HFIP at ambient temperature. variety nitro‐bearing ]isoquinoline derivatives efficiently prepared poor to quantitative yields (28–98 %). These products can be easily transformed primary amines and amide by simple chemical reactions. Treatment other nitrogen‐containing heterocycles such pyrrolo[1,2‐ ]quinoline substituted indoles under this developed reaction system afforded N ‐heterocycles relatively lower (15–19

Язык: Английский

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Regioselective C(sp2)-H Nitrosation and Nitration of (Hetero)arenes with Fe(NO3)3·9H2O as Promoter, Nitroso and Nitro Source

Tetrahedron, Год журнала: 2024, Номер unknown, С. 134329 - 134329

Опубликована: Окт. 1, 2024

Язык: Английский

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Selective C6‐Nitration of Benzothiazolones with Iron Nitrate

ChemistrySelect, Год журнала: 2024, Номер 9(41)

Опубликована: Окт. 29, 2024

Abstract We report here a selective C6‐nitration of benzothiazolones in the presence iron nitrate as nitro source. A series novel 6‐nitrobenzothiazolin‐2‐one derivatives were prepared with moderate to excellent yields at room temperature. The method shows good regioselectivity, broad substrate scope and compatibility functional groups. Further transformations performed for reduction groups, amination carbonyl groups alkylation amine 3‐position product.

Язык: Английский

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