Merging Photoinduced Electron Transfer with Hydrogen Atom Transfer: Formal β-C(sp³)–H Pyridination of Carbonyls

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

Published: Jan. 9, 2025

In this study, a novel approach that combines photoinduced electron transfer (ET) with hydrogen atom (HAT) has been introduced for the selective β-C(sp3)–H pyridination of carbonyl compounds. This method is notable its absence transition metals and ability to function under benign reaction conditions, resulting in range pyridinated derivatives consistently moderate good yields. The significance technique further underscored by potential late-stage functionalization pharmaceutically significant molecules. Mechanistic investigations confirmed proceeds via radical-mediated pathway.

Language: Английский

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1,2-Acylphosphinylation of Styrenes to Access β-Aryl-γ-ketophosphine Oxides by Irradiation-Induced Radical Relay

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

Published: March 11, 2025

An acylphosphinylation reaction has been devised for the synthesis of β-aryl-γ-ketophosphine oxides, employing styrenes and acyl azolium salts through an irradiation-induced radical relay mechanism. This method effectively constructs C–C C–P bonds while demonstrating excellent functional group tolerance. Mechanistic studies revealed that a radical-addition–coupling–elimination cascade process was involved in this reaction.

Language: Английский

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Direct Alkene Functionalization via Photocatalytic Hydrogen Atom Transfer from C(sp3)–H Compounds: A Route to Pharmaceutically Important Molecules

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Direct functionalization of alkenes with C(sp

Language: Английский

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Light-Driven Formate-Salts-Induced Cleavage of Oxidized Lignin Model Compounds

Organic Letters, Journal Year: 2024, Volume and Issue: 26(39), P. 8249 - 8253

Published: Sept. 24, 2024

We report a light-induced cleavage of oxidized lignin model compounds utilizing formate salts. For containing an aliphatic hydroxyl (γ-OH) group, the employment hydrogen atom transfer (HAT) catalyst was crucial to preserving efficacy fragmentation reaction. Furthermore, we successfully converted trimeric compound into desired products with moderate yields.

Language: Английский

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Cu‐Catalyzed Coupling of Sulfonyl Chlorides with Alkenes: Synthesis of Dienyl Sulfones and β‐Chlorosulfones

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 14, 2024

Abstract This work reports a Cu‐catalyzed coupling technique for synthesizing ( E )‐dienyl sulfones and β‐chlorosulfones from 1‐arylbutadienes styrenes, respectively. By employing easily available inexpensive reagents, this method enables the synthesis of diverse array dienyl with excellent functional group tolerance under base‐ oxidant‐free conditions. It also proves versatile late‐stage functionalization drug molecules scale‐up reactions. The showcases notable selectivity, gentle reaction conditions, compatibility various groups as demonstrated through 66 examples display regioselectivity.

Language: Английский

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Dicarbofunctionalization of Vinylarenes with Pyridine and Aldehydes via Photocatalytic Hydrogen Atom Transfer

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15877 - 15883

Published: Oct. 14, 2024

We describe a metal-free and mild three-component reaction utilizing vinylarenes, alkyl aldehydes, 4-cyanopyridine. In this reaction, the scope of vinylarenes aldehydes includes over 40 examples, generating variety β-pyridinyl ketones. Moreover, potential applications method have been demonstrated by functionalization pharmaceutical molecules. An acyl radical is proposed to be produced via polarity-matched hydrogen atom transfer between triplet-state diradical from benzophenone.

Language: Английский

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