Visible-Light-Irradiated Cascade Reaction of Indole-Tethered Alkenes to Access Tetracyclic Tetrahydro-γ-carbolines

Organic Letters, Год журнала: 2022, Номер 24(14), С. 2630 - 2635

Опубликована: Март 30, 2022

A series of indole-derived alkenes have been designed and applied in a photocatalytic cascade reaction with bromodifluoroacetate esters, affording an unknown type tetracyclic tetrahydro-γ-carboline derivative up to 90% yields. Mechanistic studies suggest that the proceeds as key intermediate. The tolerates diverse pool substrates, which provides efficient method for construction compounds.

Язык: Английский

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Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 212 - 219

Опубликована: Фев. 2, 2024

An efficient multicomponent reaction of newly designed β-trifluoromethyl β-diazo esters, acetonitrile, and carboxylic acids via an interrupted esterification process under copper-catalyzed conditions has been developed, which affords various unsymmetrical N , -diacyl-β-amino esters in good to excellent yields. The features mild conditions, a wide scope β-amino acids, also applicability large-scale synthesis, thus providing way for the synthesis β-diacylamino esters. Furthermore, this represents first example Mumm rearrangement

Язык: Английский

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Intramolecular Appel Reaction of Trifluoromethylated β-Keto Diazos Enabling Assembly of Trifluoromethylpyrazoles

Organic Letters, Год журнала: 2022, Номер 24(11), С. 2258 - 2263

Опубликована: Март 17, 2022

A method for the generation of trifluoromethylated β-keto diazos and their applications in intramolecular Appel type reactions are reported. The key success this reaction is a diazo species as an N-nucleophile reactions. This conducted under mild conditions has broad substrate scope, affording trifluoromethylpyrazoles ≤94% yields. protocol represents new also mode fluoro diazoalkanes.

Язык: Английский

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Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Язык: Английский

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A DFT study of Ni-catalyzed (3 + 3)-annulation between donor–acceptor cyclopropanes and diaziridines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(8), С. 1948 - 1958

Опубликована: Янв. 1, 2023

The mechanism and stereoselectivity of the Ni-catalyzed [3 + 3] annulation between donor–acceptor cyclopropanes (DACs) diaziridines were rationalized by DFT calculations.

Язык: Английский

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Rh‐Catalyzed Hydration/C−F Bond Cleavage of Fluorinated Diazoalkanes Enabling Synthesis of α‐Fluoro‐β‐ketophosphonates

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(17), С. 2883 - 2887

Опубликована: Июль 21, 2023

Abstract (β‐Diazo‐α,α‐difluoroethyl)phosphonates have been emerging as useful building blocks in organic synthetic chemistry recent years, which can be used diazo analog or masked carbene for the rapid assembly of difluoromethylene phosphonate‐containing compounds. Herein, we elaborate a method synthesis α‐fluoro‐β‐ketophosphonates from hydration/C−F bond cleavage situ generated (β‐amino‐α,α‐difluoroethyl)phosphonates via Rh‐carbene intermediate. Divers are tolerated this reaction affording good yields. This water coupling partner, represents (β‐diazo‐α,α‐difluoroethyl)phosphonates and also generating bioactive α‐fluoro‐β‐ketophosphonates.

Язык: Английский

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Synthesis, biological evaluations and in silico studies on pyrimidine-appended fused pyrazolones as anticancer and antimicrobial agents

Journal of Molecular Structure, Год журнала: 2023, Номер 1296, С. 136759 - 136759

Опубликована: Окт. 4, 2023

Язык: Английский

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A bioactive sprite: Recent advances in the application of vinyl sulfones in drug design and organic synthesis

Life Sciences, Год журнала: 2024, Номер 352, С. 122904 - 122904

Опубликована: Июль 9, 2024

Язык: Английский

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Esterification of Carboxylic Acids with (β-Diazo-α,α-difluoroethyl)phosphonates under Photochemical Conditions

Acta Chimica Sinica, Год журнала: 2021, Номер 79(6), С. 747 - 747

Опубликована: Янв. 1, 2021

a ( 江苏省林业资源高效加工利用协调创新中心 化学工程学院 南京林业大学 南京 210037) b 生命科学与化学学院 不来梅雅各布大学 不来梅 28759) 摘要 利用可见光促进的 O-H 插入反应可以在温和条件下实现羧酸与原位生成的(β-重氮-α,α-二氟乙基)膦酸酯的酯化 反应, 以良好的产率得到了含有 α,α-二氟甲基膦酸酯的羧酸酯类化合物. 该反应操作简单, 对于不同的官能团具有良 好的适应性.因此, 这一反应为 α,α-二氟甲基膦酸酯衍生物的合成提供了一种高效的策略.关键词 二氟重氮乙烷; (β-重氮-α,α-二氟乙基)膦酸酯; 可见光促进;

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Ru-Catalyzed Hydrogen Atom Transfer/C–F Bond Cleavage of Difluoroalkyl Diazos with Hantzsch Ester via a Photocatalytic Radical Process

Organic Letters, Год журнала: 2022, Номер 24(43), С. 8036 - 8040

Опубликована: Окт. 26, 2022

A Ru-catalyzed reaction of difluoroalkyl diazo compounds with Hantzsch ester under visible light to achieve the formation α-fluorovinylphosphonates via a radical process has been developed. Mechanistic experiments and density functional theory calculations reveal that generation carbon is directly through hydrogen atom transfer (HAT) by ester. This system represents first example radicals from Hantzsch-ester-assisted HAT also demonstrates new radical-involved pathway for compounds.

Язык: Английский

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