Visible light-induced synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane ketonesviacooperative photoredox and N-heterocyclic carbene catalysis

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3909 - 3915

Published: Jan. 1, 2023

Visible light-induced highly efficient synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane with mild conditions, high atom economy, and superior functional group tolerance.

Language: Английский

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Nitrene transfer reaction with hydroxylamine derivatives

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(14), P. 1889 - 1906

Published: Jan. 1, 2023

Recent progress on catalytic nitrene transfer reactions with hydroxylamine derivatives as prevalent precursors is summarized in this highlight.

Language: Английский

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Homogeneous Iron Catalyzed C−H Amination

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 6, 2024

Abstract Iron‐catalyzed C−H amination is emerging as an attractive and sustainable method to install amine functionalities into organic compounds. Amination of C( sp 3 )−H bonds usually mediated by iron‐nitrene intermediate via a Hydrogen Atom Abstraction/Radical Recombination mechanism reminiscent biomimetic oxidation. Accordingly, this transformation can be catalyzed engineered iron enzymes, heme nonheme complexes well salts, although it often limited intramolecular reactions and/or activated positions. Aromatic 2 addition electrophilic nitrenes or protonated N‐radical intermediates (produced with Fe catalysts) aromatic systems. Again, high selectivity obtained (pseudo) reactions. From mechanistic perspective, several nitrene have been isolated characterized over the years in different ligand scaffolds oxidation states. Structure‐activity correlations drawn only few cases point key role spin density on state. This review describes state art for homogeneous focusing last 5 (2019–2023) from mechanism‐driven catalyst design perspective.

Language: Английский

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Recent advances in transition-metal catalyzed nitrene transfer reactions with carbamates

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(3), P. 108778 - 108778

Published: July 8, 2023

Language: Английский

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Iron-catalysed nitrene transfer reaction to form C N bonds

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 144, P. 155136 - 155136

Published: June 12, 2024

Language: Английский

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Asymmetric Intramolecular Amination Catalyzed with Cp*Ir-SPDO via Nitrene Transfer for Synthesis of Spiro-Quaternary Indolinone

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(28), P. 18841 - 18847

Published: July 8, 2024

An asymmetric intramolecular spiro-amination to high steric hindering

Language: Английский

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Iron/Photosensitizer-Catalyzed Directed C–H Activation Triggered by the Formation of an Iron Metallacycle

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(7), P. 4552 - 4559

Published: March 21, 2023

C–H functionalization reactions catalyzed by iron, the most abundant transition metallic element in Earth's crust, are one of ideal synthetic methods. However, there a limited number strategies for iron-catalyzed directed activation when compared to other first-row metals. Here, we report iron/photosensitizer-catalyzed alkenylation amide derivatives via σ-CAM (σ-complex-assisted metathesis) promoted situ generation an iron metallacycle. Mechanistic experiments suggest that bond cleavage would proceed from metallacycle generated rather than oxidative addition low-valent species.

Language: Английский

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NBS-mediated C(sp³)–H amidation of N,N-dimethylamides with N-acyloxyamides

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

Published: Jan. 1, 2025

Efficient synthesis of methylenebisamides was achieved by NBS-mediated amidation C(sp 3 )–H bonds adjacent to the nitrogen in N , -dimethylamides with -acyloxyamides.

Language: Английский

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A Metal-Catalyzed Tunable Reaction of Ylides with Hydroxylamine Derivatives

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

Published: March 25, 2025

In this work, a tunable reaction of metal acyl nitrene with ylides is reported for the divergent synthesis enamides and α,α-dicarbonyl phosphorus ylides. The featured mild conditions, good efficiency, broad generality. particular, resulting could be structurally elaborated into potential useful scaffolds. Mechanism investigation suggests that formation was ascribed to nucleophilic substitution ferric sulfur It believed represents an initial example preparing from iron-catalyzed transfer.

Language: Английский

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Visible-Light-Induced Radical Cascade Cross-Coupling via C(sp³)–H Activation and C–N/N–O Cleavage: Feasible Access to Methylenebisamide Derivatives

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2300 - 2305

Published: March 27, 2023

Here we report facile and manipulable access to methylenebisamide derivatives via visible-light-driven radical cascade processes incorporating C(sp3)–H activation C–N/N–O cleavage. Mechanistic studies reveal that a traditional Ir-catalyzed photoredox pathway novel copper-induced complex-photolysis are both involved, contributing activating the inert N-methoxyamides rendering valuable bisamides. This approach exhibits many advantages, including mild reaction conditions, broad scope functional group tolerance, competitive step economy. Given mechanistic plenitude operational simplicity, believe this package deal paves promising way for synthesis of nitrogen-containing molecules.

Language: Английский

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