Photoredox-Catalyzed Alkene Acylesterification with Acyloxime Esters via C–C and Tertiary C–O Bond Formation

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

Published: Jan. 7, 2025

We describe an efficient acyl esterification method for alkenes utilizing acyloxime esters as bifunctional reagents featuring radical acylation and congested C–O bond formation. This approach is characterized by mild photoredox conditions, high step atom economy, a broad substrate scope, excellent regioselectivity. A variety of valuable α-acyl hindered alcohol esters, including those obtained via gram-scale synthesis late-stage functionalization pharmaceutical molecules, were presented, demonstrating its synthetic potential practicability.

Language: Английский

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Photoredox catalytic alkylarylation of alkynes with arylsulfonylacetate as bifunctional reagent

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(6), P. 2022 - 2028

Published: March 7, 2024

Language: Английский

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Photoredox-Catalyzed Acylchlorination of α-CF₃ Alkenes with Acyl Chloride and Application as Masked Access to β-CF₃-enones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2656 - 2661

Published: March 25, 2024

We disclose a photocatalytic strategy that simultaneously addresses the construction of trifluoromethylated quaternary carbon centers and preparation β-CF3-enones through radical difunctionalization α-CF3 alkenes with acyl chlorides. This method is characterized by its broad functional group compatibility, high efficiency, atom economy. The versatility this transformation poised to broaden applications alkenes, providing new pathways for rapid assembly structurally diverse fluorinated compounds.

Language: Английский

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Visible light-mediated metal-free alkyl Suzuki–Miyaura coupling of alkyl halides and alkenylboronic acids/esters: a green method for the synthesis of allyl difluoride derivatives

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3453 - 3461

Published: Jan. 1, 2023

Halogen bonding-assisted C sp 3 –Br homolysis and bromine radical-mediated oxidative deboronation make visible-light-driven photocatalyst-free alkyl Suzuki–Miyaura coupling of alkenylboronic acids/esters with α-bromodifluoroacylarenes accessible.

Language: Английский

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Visible-Light Photoredox-Catalyzed Divergent 1,2-Diacylation and Hydroacylation of Alkenes with Carboxylic Acid Anhydride

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5268 - 5272

Published: July 6, 2023

A photoredox-catalyzed divergent 1,2-dicarbonylation and hydroacylation of alkenes with acid anhydride is presented. This approach offers a mild efficient entry to 1,4-dicarbonyl compounds bearing all-carbon quaternary centers, exhibiting broad substrate scope high functional group compatibility. Hydrocarbonylaltion can also be realized by simply introducing proton source the reaction system. Mechanism investigations support radical addition/radical-polar crossover cascade.

Language: Английский

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Cu(ii)-mediated direct intramolecular cyclopropanation of distal olefinic acetate: access to cyclopropane-fused γ-lactones

Chemical Science, Journal Year: 2023, Volume and Issue: 14(24), P. 6663 - 6668

Published: Jan. 1, 2023

A highly atom- and step-economy diastereoselective copper-mediated direct intramolecular cyclopropanation method to synthesize cyclopropane-fused γ-lactones lactams from distal olefinic acetate was disclosed.

Language: Английский

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Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7971 - 7975

Published: Sept. 11, 2024

We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of broad spectrum highly substituted methylenecarbocycles but also introduces new mechanistic pathway with aryl group migration, surpassing conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.

Language: Английский

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Halogen‐Bond‐Promoted Hydroxyperfluoroalkylation of Olefins with Molecular Oxygen under Visible‐Light Irradiation

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: June 24, 2023

Abstract Fluorinated organic compounds are indispensable, and the development of perfluoroalkylation reaction is an important topic concern. In this paper, we present generation amine‐promoted visible‐light‐induced hydroxyperfluoroalkylation olefines using molecular oxygen as a hydroxy source. This caused by formation perfluoroalkyl radicals due to visible‐light irradiation halogen‐bonded complex tertiary amine iodide. transformation applicable for various types electron‐deficient olefins styrene, fluoroalkyl iodides acceptable well. induced, metal‐free inexpensive readily available reagents sustainable method synthesis fluorine‐containing compounds.

Language: Английский

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Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/smiles rearrangement cascade

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110253 - 110253

Published: July 1, 2024

Language: Английский

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Visible‐Light Induced Oxidative Annulation of Enamides to 2,4,5‐Trisubstituted Oxazole Skeletons

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: Jan. 18, 2023

Abstract A novel approach to various trisubstituted oxazoles (28 examples, up 88% yield) has been developed via 9 H ‐thioxanthen‐9‐one (TX) mediated oxidative annulation of N ‐acetyl enamide under visible light irradiation in the presence BF 3 ⋅ Et 2 O (2.0 equiv) and 40 mol% PhNO . This metal‐free procedure features high atom step economy, green mild conditions broad substrate scope.

Language: Английский

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