Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2891 - 2920

Опубликована: Ноя. 13, 2024

Diaryliodonium salts have become widely recognized as arylating agents in the last two decades. Both, symmetrical and unsymmetrical forms of these serve effective electrophilic reagents various organic syntheses. The use diaryliodoniums C–C carbon–heteroatom bond formations, particularly under metal-free conditions, has further enhanced popularity reagents. In this review, we concentrate on arylation reactions involving carbon other heteroatoms, encompassing rearrangement absence any metal catalyst, summarize advancements made five years.

Язык: Английский

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Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation

Опубликована: Май 15, 2024

We demonstrate 1) that halogen bonding is not critical for enabling light-driven radical generation from diaryliodonium salts and 2) radi-cals generated by this route can be captured transition-metals C–H arylation reactions. These results are the first step toward devel-oping new metal-catalyzed aryl couplings without exogenous photocatalysts.

Язык: Английский

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Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation

Chemical Communications, Год журнала: 2024, Номер 60(54), С. 6929 - 6932

Опубликована: Янв. 1, 2024

We demonstrate (1) detectable halogen bonding is not critical for enabling light-driven radical generation from diaryliodonium salts and (2) radicals generated by this route can be captured transition-metals C-H arylation reactions. These results are the first step toward developing new metal-catalyzed aryl couplings without exogenous photocatalysts.

Язык: Английский

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Organophotoredox Catalyzed C‒O Bond Cleavage: A Chemoselective Deprotection Strategy for Phenolic Ethers and Esters Driven by the Oxophilicity of Silicon

Опубликована: Март 19, 2024

An organo-photocatalyzed approach for the chemoselective dealkylation and de-esterification of phenols is developed by employing trimethyl silyl chloride as C‒O bond activator 9-Mes-10-MeAcr+ClO4‒ photoredox catalyst. This method demonstrates an exceptional selectivity towards cleavage phenolic ethers esters over equivalent aliphatic scaffolds, presenting a broad range functional group sustainability. strategy also enables selective debenzylation in presence reduction-sensitive groups. The photocatalytic efficiency was further extrapolated fragmentation lignin models synthetic modification manufacturing FLAP inhibitor. Mechanistic studies, photophysical experiments computations provide evidence involvement oxonium intermediate, generated through photo-oxidation arene ring, which ultimately leads to disintegration bond, facilitated oxophilicity silicon.

Язык: Английский

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Sulfur-Promoted Access to 3-Arylquinoxalin-2-ones by Oxidative Coupling of o-Phenylenediamines with Arylacetates

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6098 - 6102

Опубликована: Июль 15, 2024

We disclose the synthesis of 3-arylquinoxalin-2-ones from o-phenylenediamines and readily available arylacetates. The method harnesses selective oxidative property elemental sulfur in presence amine base catalyst DMSO. reactions are operationally simple tolerate a wide range functional groups.

Язык: Английский

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