Stereoselective Synthesis of Axially Chiral Allenes and Styrenes via Chiral Phosphoric Acid Catalysis: An Overview

ACS Omega, Journal Year: 2024, Volume and Issue: 9(31), P. 33351 - 33364

Published: July 26, 2024

Chiral allenes and styrenes are essential components in fields like medicinal chemistry, materials science, organic synthesis. They serve a crucial role as chiral ligands catalysts asymmetric Over the past decade, there has been significant advancement development of practical methods utilizing organocatalytic strategies for synthesis styrenes. It is noteworthy that despite extensive studies on formation styrenes, existing reviews their construction confined to specific organocatalysis, called phosphoric acid catalysis, less documented. This review aims explore different conceptual approaches based electrophilic species involved reaction produce stereoselective providing insights into recent advancements field. Emphasis placed works published since 2017, with detailed discussions mechanisms examples from literature.

Language: Английский

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Ph₃P═O-Catalyzed Reductive Deoxygenation of Alcohols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 16022 - 16027

Published: Oct. 11, 2024

Reductive deoxygenation of alcohols is particularly challenging because the high bond dissociation energy C–OH and poor leaving ability hydroxyl group. Herein we describe a Ph3P═O-catalyzed reductive benzyl with PhSiH3 under an air atmosphere within 30 min reaction time. The use catalytic loading Ph3P═O enhances practicality this protocol.

Language: Английский

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Modular Assembly of Acridines by Integrating Photo‐Excitation of o‐Alkyl Nitroarenes with Copper‐Promoted Cascade Annulation

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: July 23, 2024

Abstract Acridine frameworks stand as pivotal architectural elements in pharmaceuticals and photocatalytic applications, owing to their chemical adaptability, biological activity, unique excited‐state dynamics. Conventional synthetic routes often entail specialized starting materials, anaerobic or moisture‐free conditions, elaborate multi‐stage manipulations for incorporating diverse functionalities. Herein, we present a convergent approach integrating photo‐excitation of readily available ortho ‐alkyl nitroarenes with copper‐promoted cascade annulation. This innovative system enables an aerobic, one‐pot reaction o‐ alkyl arylboronic acids, thereby streamlining the modular construction wide array acridine derivatives various functional groups. encompasses symmetrical, unsymmetrical polysubstituted varieties, some which are otherwise exceptionally difficult synthesize. Furthermore, it significantly improves production structurally varied acridinium salts, featuring enhanced photophysical properties, high excited state potentials ( E * red =2.08–3.15 V), exhibiting superior performance intricate photoredox transformations.

Language: Английский

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Modular Assembly of Acridines by Integrating Photo‐Excitation of o‐Alkyl Nitroarenes with Copper‐Promoted Cascade Annulation

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(42)

Published: July 23, 2024

Abstract Acridine frameworks stand as pivotal architectural elements in pharmaceuticals and photocatalytic applications, owing to their chemical adaptability, biological activity, unique excited‐state dynamics. Conventional synthetic routes often entail specialized starting materials, anaerobic or moisture‐free conditions, elaborate multi‐stage manipulations for incorporating diverse functionalities. Herein, we present a convergent approach integrating photo‐excitation of readily available ortho ‐alkyl nitroarenes with copper‐promoted cascade annulation. This innovative system enables an aerobic, one‐pot reaction o‐ alkyl arylboronic acids, thereby streamlining the modular construction wide array acridine derivatives various functional groups. encompasses symmetrical, unsymmetrical polysubstituted varieties, some which are otherwise exceptionally difficult synthesize. Furthermore, it significantly improves production structurally varied acridinium salts, featuring enhanced photophysical properties, high excited state potentials ( E * red =2.08–3.15 V), exhibiting superior performance intricate photoredox transformations.

Language: Английский

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Advances in Catalytic Asymmetric Hydrogen-Phosphine/Phosphorus Functionalization of Unsaturated Carbon-Carbon Bonds

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(12), P. 3647 - 3647

Published: Jan. 1, 2024

Language: Английский

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