Synthesis of CF₃–Isoquinolinones and Imidazole-Fused CF₃–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10180 - 10196

Published: July 4, 2024

Presented herein are novel syntheses of CF

Language: Английский

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Reverse Regioselective Cp*Co(III)-Catalyzed [4 + 2] C–H Annulation of N-Chloroamides with Vinylsilanes: Synthesis of 4-Silylated Isoquinolones and Their Synthetic Utilities

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7878 - 7883

Published: Oct. 23, 2023

We have developed a Cp*Co(III)-catalyzed reverse regioselective [4 + 2] annulation of N-chlorobenzamides/acrylamides with vinylsilanes for the synthesis 4-silylated isoquinolones. The reaction was performed at ambient temperature under redox-neutral conditions. utilized N-Cl bond as an internal oxidant, furnished required products excellent regioselectivities, and demonstrated high functional group tolerance. synthetic utility isoquinolones has been preparation 4-heteroarylated 4-alkylated via metal-free C-C couplings. Additionally, 3,4-dihydroisoquinolones were synthesized protodesilylation isoquinolones, thus making vinylsilane ethylene surrogate.

Language: Английский

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Harnessing Dual Reactivity of N-Chloroamides for Cascade C–H Amidation/Chlorination of Indoles under Cobalt-Catalysis: Overriding Hofmann Rearrangement Pathway Leading to Aminocarbonylation

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 27, 2024

Herein, we have developed a Cp*Co(III)-catalyzed cascade C-2 amidation/C-3 chlorination of indoles by leveraging the dual functionality

Language: Английский

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Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4458 - 4494

Published: Nov. 24, 2023

Abstract The preservation of scarce rare earth metals, such as palladium, rhodium, iridium, and others, poses a significant challenge for humanity due to their limited availability. These metals might be replaced by earth‐abundant 3d‐transition cobalt, manganese, iron, nickel, copper, etc . Isoquinolines have acquired an important position in synthetic organic chemistry well medicinal chemistry. They manifest diverse range natural molecules, serving pivotal synthons the synthesis numerous bioactive compounds with notable significance. Numerous reports on isoquinoline derivatives via transition metal catalysis been published worldwide. In this review, we summarize recent approaches synthesizing various using 3d‐transition‐metal catalysts since 2020. review has divided into different 3d‐transition‐metal‐based catalysis. We expect that will bring better overview present status progress made isoquinolines persuade more advancements research area near future.

Language: Английский

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Co(III) ‐Catalyzed Regioselective [4+2]‐Annulation of N‐Chlorobenzamide with Allenes and Vinyl Acetate

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 28, 2023

Abstract A regioselective annulation protocol of N ‐chlorobenzamide with allenes and vinyl acetate is reported using a less expensive catalytic system, i. e . Co(III) catalysis Na 2 CO 3 as base. (CO) NH−Cl acts both, an internal oxidant directing group. Allenes are successfully annulated ‐chlorobenzamide, providing different exocyclic isoquinolone derivatives in good to moderate yield. Notably, acetylene surrogate undergoes the developed provide excellent Interestingly, situ deprotection acetyl group allowed quantitative synthesis hydroxyisoquinolone.

Language: Английский

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Ru(II)-Catalyzed Redox-Neutral C–H Olefination and Tandem Cyclization with Vinyl Sulfones: Leveraging Sulfinate Anion as a Leaving Group for the Synthesis of 3-Methyleneisoindolin-1-ones

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

We developed a Ru(II)-catalyzed redox-neutral C–H olefination of N-methoxybenzamides with vinyl sulfones. The reaction is operationally simple and conducted at ambient temperature does not require silver additives or external oxidants, making it suitable for late-stage functionalization. Notably, we leveraged the leaving group ability sulfinate anion to synthesize 3-methyleneisoindolin-1-ones through tandem olefination/cyclization/elimination sequence temperature. Moreover, successfully demonstrated synthetic versatility 3-methyleneisoindolin-1-one construction an isoindolobenzazepine core.

Language: Английский

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Solvent-Driven Room-Temperature Curtius Rearrangements to Access Nucleotides Bearing Substituted Fused Pyridones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4356 - 4360

Published: May 13, 2024

The intramolecular Curtius rearrangement suffers from a high reaction temperature, low yields, tedious product isolation, and difficult scale up. This study presents room-temperature that can be novelly driven by the HFIP solvent, followed light-illuminated cyclization. Such mild allows for preparation of various fused pyridone derivatives with diverse substituent groups have rarely been incorporated previous methods. roles light are investigated set control experiments through combination IR NMR titration. Furthermore, using substituted pyridones as unnatural bases, we obtain panel new nucleotides.

Language: Английский

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