Synthesis of Indenone Derivatives by Rh(III)-Catalyzed C–H Functionalization of Sulfoxonium Ylides with 1,3-Diynes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(18), P. 3395 - 3400

Published: May 5, 2022

The transition-metal-catalyzed C-H functionalization of sulfoxonium ylides with alkynes formally participates in [4 + 2] annulations to deliver the naphthol scaffolds. In contrast, herein we disclose first Rh(III)-catalyzed activation, followed by redox-neutral [3 annulation 1,3-diynes, which delivers alkynated indenone derivatives. This protocol features a good functional group tolerance, broad substrate scope, moderate excellent yields, and mild reaction conditions. mechanism was supported through ESI-HRMS characterizing key intermediates catalytic cycle.

Language: Английский

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Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1457 - 1464

Published: April 14, 2023

Abstract In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides N ‐carbamoylindoles with carbonate was accomplished, which afforded a series naphthalenones containing β‐ketosulfoxonium ylide moiety, isocoumarins, pyrimidones. This protocol featured mild conditions, broad substrate scope, functional‐groups compatibility. addition, related applications preliminary mechanistic exploratory were also investigated magnified image

Language: Английский

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α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(5), P. 879 - 909

Published: Dec. 6, 2022

Transition metal-catalyzed cross-coupling of sp2 C-H bonds with diazo compounds via carbene migratory insertion represents an efficient strategy for the construction C-C and C-heteroatom in organic synthesis. Despite popularity as coupling partners activation, they pose serious safety stability issues due to potential exothermic reactions linked release N2 gas. However, compared compounds, sulfoxonium ylides are generally crystalline solids, more stable, widely used industrial scales, easier/safer prepare. Therefore, recent years have witnessed upsurge employing α-carbonyl alternative surrogate transition activation. Unlike contain inherent serve a partner well weak directing group. This review will summarize progress made both categories reactions.

Language: Английский

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Transition metal-catalyzed C–H/C–C activation and coupling with 1,3-diyne

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(14), P. 2842 - 2869

Published: Jan. 1, 2023

The 1,3-diynes hold a prominent position among the many coupling partners employed in metal-catalysed C–H activation because of their ability to form complex bis-heterocycles one shot.

Language: Английский

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Redox-neutral C–H annulation strategies for the synthesis of heterocycles via high-valent Cp*Co(iii) catalysis

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(19), P. 3918 - 3941

Published: Jan. 1, 2023

This review demonstrates the redox-neutral synthetic approaches towards valuable heterocycles such as isoquinolines, indoles, isoquinolones, and tetrahydroquinolines via high-valent Cp*Co( iii ) catalysis.

Language: Английский

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Divergent Synthesis of Trifluoromethyl-Substituted 1,2-Dihydroquinoxalines and Diimines by Cascade Reactions of CF₃–Imidoyl Sulfoxonium Ylides with Azo Compounds

Organic Letters, Journal Year: 2023, Volume and Issue: 25(38), P. 7046 - 7050

Published: Sept. 18, 2023

A base-mediated cascade reaction of CF3-imidoyl sulfoxonium ylides and azo compounds has been achieved, allowing for facile access to trifluoromethyl-substituted 1,2-dihydroquinoxalines diimines in moderate excellent yields. Noteworthy is that the unusual N-N bond cleavage rearrangement are involved transformations.

Language: Английский

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Co(III)-Catalyzed Regioselective Benzannulation of Substituted Pyridones with 1,6-Diynes via Dual C-H Bond Activation

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(63), P. 8296 - 8299

Published: Jan. 1, 2024

A Co(III)-catalyzed site-selective C5 and C6 benzannulation of substituted pyridones with 1,6-diynes

Language: Английский

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Rh(III)-catalyzed [4+1] annulation of sulfoxonium ylide with allyl alkyl ethers: A detailed theoretical study of DFT, anti-inflammatory and antidiabetic activity

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(36), P. 15989 - 15999

Published: Jan. 1, 2024

The [4+1] annulation of sulfoxonium ylides with allyl ether, catalyzed by Rh( iii ), efficiently produces alkyl-substituted indanone a broad substrate scope and excellent yield.

Language: Английский

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Switching the Reactivity of the Nickel-Catalyzed Reaction of 2-Pyridones with Alkynes: Easy Access to Polyaryl/Polyalkyl Quinolinones

Organic Letters, Journal Year: 2022, Volume and Issue: 24(33), P. 6122 - 6127

Published: Aug. 11, 2022

A Ni-catalyzed C6 followed by C5 cascade C-H activation/[2 + 2 2] annulation of 2-pyridone with alkynes has been achieved. change in the reaction pathway was achieved tuning conditions and incorporating a directing group. wide variety substrates are amenable to this transformation. The key success for transformation is use sodium iodide as an additive. More importantly, we detected five-membered metallacycle intermediate through HRMS wherein ligated metal.

Language: Английский

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Co(III)-Catalyzed Three-Component Assembling of 2-Pyridones with Dienes and Formaldehyde via C–H Bond Activation

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Here, we have demonstrated a Co(III)-catalyzed C–H functionalization of substituted pyridones with dienes and para-formaldehyde via three-component sequential reaction. A library homoallylic alcohols is synthesized high regio- chemoselectivity. The reaction scope widely compatible various N-pyridyl-2-pyridones, butadiene, dienes. Interestingly, N-pyridyl-4-pyridone also participated in the product was further converted into dihydrofuran-derived N-pyridyl-2-pyridone derivatives. convincing mechanism mechanistic investigations are described to justify current methodology.

Language: Английский

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