Recent advances in three-component radical acylative difunctionalization of unsaturated carbon–carbon bonds

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4488 - 4515

Опубликована: Янв. 1, 2023

This review highlights the recent advances in radical acylated difunctionalization of unsaturated carbon–carbon bonds and focuses on mechanistic insights these transformations.

Язык: Английский

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Energy-Transfer-Enabled Radical Acylation Using Free Alkyl Boronic Acids through Photo and NHC Dual Catalysis

ACS Catalysis, Год журнала: 2024, Номер 14(5), С. 3181 - 3190

Опубликована: Фев. 14, 2024

Cross-coupling reactions have been well received as one of the most popular protocols for ketone synthesis. As an important coupling partner, bench-stable and commercially available alkyl boronic acids are widely used in transition metal catalysis, but they rarely utilized radical precursors acylative reactions. Herein, we reported energy-transfer-enabled acylation using free via NHC/photo dual catalysis. This protocol could efficiently promote Suzuki-type cross-coupling between acyl imidazoles multicomponent alkylacylations alkenes, thus producing various ketones with structural diversity. Additionally, products can readily transform into a large number structurally interesting fine chemicals. Preliminary mechanistic studies shed light on unique reaction mechanism.

Язык: Английский

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N -Heterocyclic carbene catalytic 1,2-boron migrative acylation accelerated by photocatalysis

Science Advances, Год журнала: 2024, Номер 10(30)

Опубликована: Июль 24, 2024

The transformation of organoboron compounds plays an important role in synthetic chemistry, and recent advancements boron-migration reactions have garnered considerable attention. Here, we report unprecedented 1,2-boron migrative acylation upon photocatalysis-facilitated

Язык: Английский

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Cross‐Coupling Reaction of Alkyl Halides with Aldehydes through NHC Catalysis

ChemCatChem, Год журнала: 2024, Номер 16(15)

Опубликована: Фев. 21, 2024

Abstract During the past decades, N ‐heterocyclic carbene (NHC)‐catalyzed reactions have emerged as a versatile tool in synthetic chemistry. In particular, NHC‐catalyzed cross‐coupling reaction has been significantly developed many respects, including new development and mechanistic investigation. This concept article presents recent advances towards direct of aldehydes with alkyl halides enabled by NHC organocatalysis.

Язык: Английский

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Phosphonylacylation of Alkenes Enabled by Visible-Light-Induced N-Heterocyclic Carbene Catalysis

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1711 - 1717

Опубликована: Фев. 20, 2024

Herein, we report the phosphonylacylation of alkenes via visible-light-induced N-heterocyclic carbene (NHC) catalysis to afford a series γ-ketophosphonates in moderate good yields. This protocol features mild conditions, free photocatalyst, and compatibility functional groups. The excited Breslow enolate intermediate was proposed undergo single-electron transfer with oxime phosphonate generate corresponding ketyl radical phosphonyl radical.

Язык: Английский

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Visible-light-driven four-component diacylation of styrenes with acyl azolium salts: carbonylative synthesis of 1,4-diketones

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 21, 2025

Язык: Английский

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Synthesis of 1,4-Diketones from Esters Enabled by a Tetraborylethane Reagent

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 25, 2025

A modular synthesis method for 1,4-diketones has been developed. Utilizing inexpensive carboxylic acid esters as carbonyl sources and tetraborylethane (TBE) a nucleophilic reagent, one-pot strategy constructing two C-C bonds was established. Notably, this reaction proceeds without the involvement of transition metals exhibits excellent functional group compatibility. diverse array α-substituted were synthesized using various electrophiles capture.

Язык: Английский

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N‐Heterocyclic Carbene Organocatalysis Enabled Modular Synthesis of Fluorinated Isoflavonoids to Suppress Proliferation and Migration in Breast Cancer Cells

Advanced Science, Год журнала: 2025, Номер unknown

Опубликована: Фев. 13, 2025

Abstract Isoflavonoids represent a privileged scaffold among various bioactive natural products, rendering their structural diversification through green synthesis and subsequent biological evaluations compelling research area. In this study, an NHC organocatalytic radical acylalkylation of 1,3‐enynes using salicylaldehydes is presented, followed by cascade intramolecular annulation, yielding series fluorinated isoflavone derivatives with substantial yields under environmental‐friendly conditions. This approach, distinguished its excellent modularity high functional group tolerance, represents unprecedented 1,3,4‐trifunctionalization designed for the isoflavones in single step. Furthermore, it demonstrated that these synthesized isoflavonoids effectively suppress proliferation breast cancer cells, most potent compound 8 also inhibiting migration MDA‐MB‐231 cells.

Язык: Английский

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Highly Selective 1,4-Diacylation/Cycloisomerization of 1,3-Enynes: De Novo Synthetic Strategy to Polysubstituted Furans

Organic Letters, Год журнала: 2023, Номер 26(1), С. 35 - 40

Опубликована: Дек. 20, 2023

The development of a de novo synthetic strategy for rapid assembly biologically relevant multisubstituted furans is an appealing but challenging task. Herein, we disclose NHC and organophotocatalysis cocatalyzed three-component radical 1,4-diacylation/cycloisomerization cascade process readily available 1,3-enynes, which provides efficient straightforward entry to wide range polysubstituted with good yields excellent regio- chemoselectivities. reaction features mild conditions, broad substrate scopes, functional group compatibilities.

Язык: Английский

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Efficient Functionalization of Organosulfones via Photoredox Catalysis: Direct Incorporation of α-Carbonyl Alkyl Side Chains into α-Allyl-β-Ketosulfones

Molecules, Год журнала: 2024, Номер 29(9), С. 1971 - 1971

Опубликована: Апрель 25, 2024

A novel and efficient method for functionalizing organosulfones has been established, utilizing a visible-light-driven intermolecular radical cascade cyclization of α-allyl-β-ketosulfones. This process employs fac-Ir(ppy)3 as the photoredox catalyst α-carbonyl alkyl bromide oxidizing agent. Via this approach, substrates experience addition radicals to alkene bonds, initiating sequence C-C bond formations that culminate in production organosulfone derivatives. Notably, technique features gentle reaction conditions an exceptional compatibility with wide array functional groups, making it versatile valuable field organic synthesis.

Язык: Английский

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