Visible-Light-Induced Esterification of Carboxylic Acids with Arylsulfonium Salts

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

Published: Jan. 26, 2025

A photoinduced copper-mediated acyloxylation of arylthianthrenium or arylphenoxathiinium salts with either aliphatic aromatic carboxylic acids is described for the convenient synthesis O-aryl esters. The reaction has shown obvious advantages, such as high efficiency, good functional group tolerance, excellent chemoselectivity, and capacity esterification complex drug molecules, offering a practical synthetic route to multifunctionalized sterically congested esters, which are potentially useful in development new prodrugs twin drugs.

Language: Английский

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Visible-Light-Induced Phosphorothioation of Alkenyl Sulfonium Salts with S₈ and H-Phosphonates

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

Published: Feb. 4, 2025

An efficient and practical method for synthesizing vinyl phosphorothioates has been demonstrated through a visible-light-induced three-component reaction of alkenyl sulfonium salts, S8, H-phosphonates. This facilitates the synthesis diverse range with wide substrate scope functional group tolerance. Preliminary mechanistic studies suggest that involves phosphorothioate radical-triggered process.

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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Site-Selective Copper–N-Heterocyclic Carbene-Catalyzed C(sp²)–C(sp) Cross-Coupling of Aryl Thianthrenium Salts

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

Published: March 23, 2025

This work demonstrates Cu–NHC (NHC = N-heterocyclic carbene) catalyzed alkynylation of aryl thianthrenium salts via thiazol-2-ylidene ligands, achieving a Pd-free Sonogashira coupling with broad substrate compatibility and functional group tolerance. Late-stage pharmaceutical rare alkynylative C–H functionalization/ring-opening pathways are enabled. Thiazol-2-ylidenes, featuring "half-umbrella"-shaped geometry, exhibit superior catalytic performance over traditional imidazol-2-ylidenes, underscoring their unique ligand efficacy. catalysis enables the use as versatile electrophiles for diverse cross-couplings under mild conditions.

Language: Английский

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New Frontiers in Phosphorothioate Formation: Harnessing Inorganic Phosphorus Sources

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(99), P. 14691 - 14702

Published: Jan. 1, 2024

This review highlights the latest advancements in synthesis of phosphorothioates and their derivatives from inorganic phosphorus sources, focusing on applicability, mechanisms, current limitations, potential future directions.

Language: Английский

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