Gold/Silver-Catalyzed Synthesis of Functionalized Indoles from N-Allyl-2-Alkynylanilines and α-Diazo Compounds via 1,3-Allyl Migration

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An unprecedented gold catalyzed synthesis of functionalized indoles from N -allyl-2-(aryl/alkylethynyl)anilines (1,7-enynes) and α-diazo compounds has been developed.

Language: Английский

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A Regioselective Ruthenium‐Catalyzed Oxidative C–H Alkenylation of 2‐Aryl‐4H‐Benzo[d][1,3] Oxazin‐4‐Ones

Applied Organometallic Chemistry, Journal Year: 2025, Volume and Issue: 39(6)

Published: May 2, 2025

ABSTRACT 2‐Aryl‐ 4H ‐benzo[ d ][ 1 , 3 ]oxazin‐ 4 ‐one derivatives can be directly alkenylated with alkyl acrylates using a facile Ru (II)‐catalyzed process; Cu (OAc) 2 •H O as an oxidizer through formation of pentagon cyclic complex imine‐Ru (II) for C–H activation is described. The unique catalytic reaction well matched miscellaneous olefins such vinyl ketones, acrylonitrile, and acrylates. aryl rings bearing electronically diverse substituents tolerated the conditions to provide ortho‐alkenylation products in high regioselectivities admissible yields.

Language: Английский

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Rhodium‐Catalyzed C(sp³)–H Arylation of 8‐Methylquinolines with Arylsilanes

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(21), P. 2627 - 2632

Published: July 9, 2024

Comprehensive Summary We herein describe a Cp*Rh III ‐catalyzed C(sp 3 )–H mono‐arylation of 8‐methylquinolines with benign arylsilanes. The use 1‐adamantane carboxylic acid can benefit the efficiency in this transformation, and AgF was both activator reoxidant. Control experiments indicated inability C—H cleavage determining rate reaction.

Language: Английский

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Transition Metal‐Catalyzed C−H Activation/Functionalization of 8‐Methylquinolines

The Chemical Record, Journal Year: 2024, Volume and Issue: 24(11)

Published: Oct. 18, 2024

Abstract 8‐Methylquinoline is regarded as an ideal substrate to participate in diversely C(sp 3 )−H functionalization reactions. The presence of the chelating nitrogen atom enables 8‐methylquinoline easily form cyclometallated complexes with various transition metals, leading selective synthesis functionalized quinolines. Considering great importance quinoline cores medicinal chemistry, this review article, we have covered publications related C−H activation and under metal catalysis during last decade.

Language: Английский

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DFT Study on the Mechanisms and Selectivities in Rh (III)-Catalyzed [5 + 1] Annulation of 2-Alkenylanilides and 2-Alkylphenols with Allenyl Acetates

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8562 - 8577

Published: June 7, 2024

The mechanisms and regio-, chemo-, stereoselectivity were theoretically investigated in the Rh(III)-catalyzed [5 + 1] annulation of 2-alkenylanilides 2-alkylphenols with allenyl acetates. Two different reactants, 2-alkylphenols, selected as model systems density functional theory calculations. obtained theoretical results show that both these reactants exhibit similar steps, namely, (1) N-H/O-H deprotonation C-H activation, (2) acetate migratory insertion, (3) β-oxygen elimination, (4) intramolecular nucleophilic addition nitrogen/oxygen-rhodium bond resulting 1]-annulation, (5) protonation formation desired product regeneration Rh(III) catalyst. evidence suggests selectivity is determined at step acetate's insertion. Moreover, regioselectivity driven by electronic effects, while interaction energies (C-H···π C-H···O interactions) play a more imperative role controlling stereoselectivity. not only well rationalize experimental observations but also provide important mechanistic insights for related types 1]-annulation reactions.

Language: Английский

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Copper-Promoted ortho-Directed C-H Amination of 2-Arylpyridines with NH-heterocycles

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(36), P. 7390 - 7394

Published: Jan. 1, 2024

Copper-mediated C–N coupling of azaheterocycles with aryl C–H bonds has been realized for the synthesis N-(hetero)arylated heteroarenes.

Language: Английский

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Efficient Accessibility of Indole and Pyrrole Nuclei via Late-Stage Aryl C-H Activation of Drug Molecules Promoted by Thianthrenium Salts

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An efficient redox-neutral palladium-catalyzed system has been developed to introduce indole and pyrrole various bioactive molecules via late-stage aryl C–H activation, providing a robust tool explore structure–activity relationships (SARs).

Language: Английский

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Palladium catalyzed C(sp3)-H alkylation of 8-methylquinolines with aziridines: access to functionalized γ-quinolinylpropylamines

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(99), P. 14818 - 14821

Published: Jan. 1, 2024

An intrinsic directing group-assisted site-selective C(sp 3 )–H alkylation of 8-methylquinolines has been accomplished using readily available aziridines and Pd( ii ) catalysis.

Language: Английский

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Ru^II–Catalyzed C–H Activated Diverse Cyclization with Transformation of Substrate-DG to Functional Groups: Synthesis of Functionalized Indoles and Indenones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(19), P. 14183 - 14196

Published: Sept. 16, 2024

We present an elegant and efficient method for Ru(II)-catalyzed C-H activation, followed by a diverse range of intermolecular cross-dehydrogenative coupling reactions. This process is facilitated intrinsic directing group (DG) includes the in situ transformation DG into common useful functional groups. Notably, this avoids installation deinstallation group. Our approach enables selective functionalization benzimidate, coupled with cyclization

Language: Английский

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