Dual iron- and organophotocatalyzed hydroformylation, hydroacylation and hydrocarboxylation of Michael-acceptors utilizing 1,3,5-trioxanes as C1-Synthone

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 10, P. 100073 - 100073

Published: April 16, 2024

A protocol based on photocatalytic cycles of both iron(III)chloride and 9,10-dicyanoanthracene (DCA) is developed for the masked hydroformylation, hydroacylation, hydrocarboxylation Michael-Acceptors utilizing readily available 1,3,5-trioxanes. Initiated by LMCT [FeCl4]– to generate chlorine radicals that promote hydrogen atom transfer (HAT) from trioxanes, used as co-photocatalyst accelerate formation desired products facilitating reoxidation iron(II) iron(III). The methodology robust, allowing generation aldehydes, ketones, carboxylic acids either altering trioxane deprotection strategy or subsequent photocatalyzed conversion initially obtained aldehydes.

Language: Английский

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Light-induced ligand-to-metal charge transfer of Fe(III)-OR species in organic synthesis

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(30), P. 6034 - 6044

Published: Jan. 1, 2024

This review highlights studies on ligand-to-metal charge transfer of Fe( iii )-OR species in organic transformations.

Language: Английский

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Embracing Heterogeneous Photocatalysis: Evolution of Photocatalysts in Annulation of Dimethylanilines and Maleimides

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(66), P. 8645 - 8657

Published: Jan. 1, 2024

Recent advances in visible-light-promoted construction of tetrahydroquinolines from dimethylanilines and maleimides are documented. Homogeneous heterogeneous photocatalytic systems, as well the reaction mechanism, emphasized. The mechanism this annulation is quite clear,

Language: Английский

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Arylcyanation of Styrenes by Photoactive Electron Donor–Acceptor Complexes/Copper Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7949 - 7955

Published: Sept. 11, 2024

A novel electron donor-acceptor (EDA) complex/copper catalysis model has been proposed for the construction of 2,3-diarylpropionitriles under visible light conditions. The developed protocol proceeds via intermolecular charge transfer between photoactive EDA complex dibutamine (DBA), aryl thianthrenium salts, and trimethylsilyl cyanide (TMSCN), followed by a copper catalytic cycle. UV-vis absorption measurements confirm participation complexes as reactive intermediates. This three-component process smoothly in presence pharmaceutically relevant core structures sensitive functional groups, which offers possibility precise editing drug molecules with important scaffolds.

Language: Английский

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Visible Light/Copper Catalysis-Enabled Arylation and Alkenylation of Phosphorothioates via Site-Selective C–H Thianthrenation

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

Published: Sept. 24, 2024

An efficient visible light/copper-enabled arylation and alkenylation of phosphorothioates with thianthrenium salts via a C(sp

Language: Английский

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Iron Photoredox Catalysis as an Effective Tool for Organic Synthesis via Visible‐Light‐Induced Homolysis (VLIH)

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(4)

Published: Jan. 1, 2025

Abstract Owing to its possible advantages for the environment and economy, photoredox catalysis of organic processes fueled by iron has garnered a lot interest recently. The potential photo‐induced single‐electron transfer (SET) events occurring outside sphere is now well acknowledged. Currently, focus shifted newly discovered photoactivation method that based on an inner‐sphere mode reactivity caused population visible‐light‐induced homolysis (VLIH) states. VLIH activation, in contrast photoredox, specific complexes, offers distinct profiles, does not require redox potentials coincide. These attractive properties have prompted development strategies use this blueprint manufacture highly reactive open‐shell species mild environments. purpose contribution promote novel synthetic techniques sustainable chemical transformations offer educational instrument understanding evolving idea.

Language: Английский

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Inorganic Bismuth Catalysts for Photocatalytic Organic Reactions

Catalysts, Journal Year: 2025, Volume and Issue: 15(2), P. 135 - 135

Published: Feb. 1, 2025

Bismuth (Bi) is recognized as a low-toxicity and environmentally friendly metal. Owing to its diverse oxidation states, Bi-based compounds demonstrate exceptional catalytic activities across numerous organic reactions. In particular, inorganic materials have emerged promising class of photocatalysts in synthetic chemistry. this review, the recent applications Bi-materials, e.g., Bi2O3, BiVO4, BiCl3, Bi2WO6, Bi4O5Br2, various reactions, including C-H oxidation, radical addition olefins, coupling been summarized. The reaction mechanisms are discussed reveal crucial steps for enhancing performance. Moreover, current challenges prospects vibrant research area also outlined, aiming provide valuable insights guidance development more efficient their pathways.

Language: Английский

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Iron-Catalyzed Ipso-Nitration of Aryl Borides via Visible-Light-Induced β-Homolysis

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3306 - 3313

Published: Feb. 7, 2025

Herein, we reported a practical method to realize ipso-nitration of boronic acids, their pinacol esters, and trifluoroborate salts with alkali metal salt NaNO3 as nitrating reagent. A FeIII/FeIV catalytic cycle involving an unusual visible-light-induced β-homolysis pathway the N–O bond in simple iron complex effectively provides nitryl radical key species. This protocol bears mild reaction conditions, broad scope (up 99% yield), good functional group compatibility, convenient scale-up synthesis.

Language: Английский

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Wavelength-Selective Reactivity of Iron(III) Halide Salts in Photocatalytic C–H Functionalization

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 24, 2025

The utility of halogen radicals in hydrocarbon functionalization extends from early examples photochemical halogenation to recent reports using photoredox catalysis with iridium complexes and simple transition metal salts such as FeCl3. majority these methods (uncatalyzed iron-catalyzed) require UV light (λ ≤ 390 nm), systematic efforts enable the use visible remain valuable. We report a Fe(III) salt that enables C–H C–C C–N under light. reactivity selectivity profile different sources demonstrates wavelength-selective behavior, which was further investigated deuterium kinetic isotope effect experiments DFT calculations. These results show control over reactive intermediates this iron-catalyzed reaction can be achieved through proper choice wavelength irradiation.

Language: Английский

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g-C₃N₄-Based Heterogeneous Photocatalyzed Synthesis and Evaluation of Antitumor Activities of Fluoroalkylated 4H-Pyrido[1,2-a]pyrimidin-4-ones

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 26, 2025

The first example of heterogeneous photoredox-catalyzed fluoroalkylation 4H-pyrido[1,2-a]pyrimidin-4-ones has been developed. With low-cost commercial g-C3N4 as the recyclable photocatalyst and cheap sodium fluoroalkyl sulfonates source, a variety fluoroalkylated pyridopyrimidinones were constructed in moderate to high yields. present reaction can be easily scaled up with good efficiency, catalytic system reused 5 times slight loss activities. Furthermore, biological activity synthesized compounds was preliminarily investigated.

Language: Английский

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