Ru(ii) catalyzed chelation assisted C(sp²)–H bond functionalization along with concomitant (4 + 2) annulation

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(27), С. 5567 - 5586

Опубликована: Янв. 1, 2023

Efficacious protocols have been established to synthesize a structurally privileged Π-extended coumarin-fused pyridone nucleus by activating the vinylic C(sp2)-H bond of coumarin-3-carboxamide under influence inexpensive Ru(II)-metal. Here an N-methoxy carboxamide entity has exploited as chelating fragment manifest functionalization with concomitant (4 + 2) annulation reaction, resulting in heterocyclic ring-forming along sulfoxonium ylide and iodonium representative bench-stable carbene surrogates. This diverse heterocycle formation via insertion strategies, is further expanded activate ortho-C(sp2)-H bonds different heterocycles employing sp2-N moiety directing group develop acyl-alkylated/alkenylated quinazolines, isoxazoles highly fluorescent pyridone-N-oxides. Intriguingly, during evaluation versatility current protocols, one-pot double C-H activation rationalized presence ylide, which results biologically potent benzimidazole-fused coumarin-centered bridge-headed polycyclic heteroarenes. Furthermore, chemo-selective late-stage synthetic transformation being designed differently substituted analogues switching nature reducing agent. In addition, photophysical experiment was done on one pyridine-N-oxide compound (7e) delightfully it exhibited fluorescence quenching activity selectively Al3+ ions, appears be unique feature our methodology. Finally, upon correlation merit developed pathways, mediated strategy superior.

Язык: Английский

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Pd-Catalyzed C-7 Arylation of Indolines with Aryltriazenes under Mild Conditions

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(15), С. 11056 - 11068

Опубликована: Июль 18, 2023

A palladium-catalyzed direct C-H arylation of indolines at C-7 position has been achieved near-ambient temperature. The reaction was carried out with aryltriazene as a stable aryl source and electron shuttle to sustainably release radical in situ under the action promoter, pyrimidine detachable directing group for synthesis 7-arylindolines oxidant- ligand-free conditions. Notably, this catalytic system can also be applied site-selective tetrahydroquinolines (C-8) carbazoles (C-1).

Язык: Английский

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Transition‐Metal‐Catalyzed Directed C−H Functionalization in/on Water

Chemistry - An Asian Journal, Год журнала: 2023, Номер 19(1)

Опубликована: Ноя. 6, 2023

Abstract Directing group assisted C−H bond functionalization using transition‐metal‐catalysis has emerged as a reliable synthetic tool for the construction of regioselective carbon‐carbon/heteroatom bonds. Off late, “in/on water directed transition‐metal‐catalysis”, though still underdeveloped, appeared one prominent themes in sustainable organic chemistry. This article covers advancements, mechanistic insights and application (hetero)arenes in/on presence transition‐metal‐catalysis.

Язык: Английский

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Discovery of Dehydroabietylamine Derivatives as Antibacterial and Antifungal Agents

Journal of Natural Products, Год журнала: 2024, Номер 87(4), С. 924 - 934

Опубликована: Март 21, 2024

A diverse array of biologically active derivatives was derived by modifying the chemically sites dehydroabietylamine. Herein, we describe synthesis a new series C-19-arylated dehydroabietylamine using palladium-catalyzed C(sp3)–H activation reaction. Five analogues (3b, 3d, 3h, 3n, and 4a) exhibited antibacterial activity against Escherichia coli. Compound 4a strong inhibitory DNA Topo II IV. Molecular docking modeling indicated that it can bind effectively to target through interactions with amino acid residues. The synthesized compounds were tested in vitro for their antifungal six common phytopathogenic fungi. mechanism action compound 4c Rhizoctorzia solani investigated, revealing disrupts morphology mycelium enhances cell membrane permeability.

Язык: Английский

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Photochemical Direct Alkylation of Heteroarenes with Alkanes, Alcohols, Amides, and Ethers

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(37), С. 7643 - 7648

Опубликована: Янв. 1, 2024

Direct functionalization of heteroarenes with simple alkanes utilizing anthracene as a photoredox catalyst has been established. This approach provides sustainable alternative, avoiding costly reagents or peroxides. The method demonstrates broad substrate scope, enabling regioselective alkylation various heteroarenes, including azoles, pyridines, quinolines, isoquinolones, and quinoxalinones under mild conditions. A range alkyl sources, such alkanes, ethers, dioxane, trioxane, alcohol, alkylamides were viable substrates. plausible catalytic cycle was proposed based on the preliminary mechanistic evidence.

Язык: Английский

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Ru‐, Rh‐ and Ir‐Catalyzed Enantioselective sp³C−H Functionalization

Chemistry - An Asian Journal, Год журнала: 2022, Номер 17(24)

Опубликована: Окт. 22, 2022

Abstract The development of novel methodologies that enable the construction complex chiral molecular scaffolds in an atom and step‐economic manner has always been area immense interest significant synthetic value. transition metal‐catalyzed enantioselective sp 3 C−H activation functionalization reactions serve as expeditious means for introducing diverse functionalities a straightforward manner. However, controlling chemo‐ stereoselectivity these is challenge owing to their ubiquity low reactivity. In this review, we present comprehensive account on recent advances inter‐ intramolecular asymmetric bond utilizing ruthenium, rhodium, iridium catalysts get insights into mechanistic aspects transformations.

Язык: Английский

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Pd-catalyzed bidentate auxiliary assisted remote C(sp³)–H functionalization

Chemical Communications, Год журнала: 2021, Номер 57(98), С. 13221 - 13233

Опубликована: Янв. 1, 2021

This article presents “state of art” trends in achieving the bidentate auxiliary assisted distal sp 3 C–H functionalization beyond proximal sites. The substrate scope and mechanistic underpinnings key methodologies are highlighted.

Язык: Английский

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The C–H functionalization of N-alkoxycarbamoyl indoles by transition metal catalysis

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(37), С. 7949 - 7969

Опубликована: Янв. 1, 2021

Indole and its congeners are ubiquitous nitrogen containing organic scaffolds found in a plethora of natural products. This review aims to highlight the transition-metal catalyzed C–H functionalization N -alkoxycarbamoyl indoles.

Язык: Английский

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Dual Metallaphotoredox‐Catalyzed Directed C(sp²)−H Functionalization: Access to C−C/C‐Heteroatom Bonds

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(39)

Опубликована: Июнь 22, 2022

Abstract Metallaphotoredox catalysis represents the combination of two activation modes: metal‐catalyzed C−H functionalization and visible‐light‐induced photocatalysis. This appealing dual technique has evolved as a versatile platform that paved way for diverse low‐energy pathways plethora synthetic transformations. The synergistic “green” approaches garnered enormous interest owing to development sustainable strategies. In recent past, significant advancements have been accomplished in constructing site‐selective C−C C‐heteroatom bonds. review outlines use photoredox directing group‐assisted reactions. mechanistic insights developments applications are addressed.

Язык: Английский

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Palladium-Catalyzed C–H Allylation/Annulation Reaction of Amides and Allylic Alcohols: Regioselective Construction of Vinyl-Substituted 3,4-Dihydroisoquinolones

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(6), С. 3871 - 3882

Опубликована: Март 2, 2023

A palladium-catalyzed highly regioselective C–H allylation/annulation reaction of N-sulfonyl amides with secondary or tertiary allylic alcohols has been developed to construct 3,4-dihydroisoquinolones bearing a synthetically valuable vinyl substituent. This cascade cyclization approach involving allylation not reported previously. The commercially available alcohol substrates, the only by-product water, and used terminal oxidant O2 provide environmentally benign advantages.

Язык: Английский

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