Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI Creative Commons
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

и другие.

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

Cu(I)‐Catalyzed Silylation and Germylation of Azauracils DOI Open Access

Frenki Mahato,

Asim Kumar Ghosh, Alakananda Hajra

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 5, 2024

The current study demonstrates a Cu(I) catalyzed direct C(sp

Язык: Английский

Процитировано

2
Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts DOI Creative Commons
Ritu Mamgain,

Kokila Sakthivel,

Fateh V. Singh

и другие.

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

Процитировано

2
Copper-Photoredox-Catalyzed Divergent Strategy for the Site-Selective Arylation and Alkylation of Glycines and Peptides DOI

Prahallad Meher,

M. Siva Prasad,

Karan Ramdas Thombare

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(24), С. 18896 - 18906

Опубликована: Дек. 12, 2024

There is a scarcity of general strategies for the site-selective α–Csp3–H arylation glycine derivatives to synthesize nonproteinogenic α-arylglycines that occur frequently in commercial drugs and bioactive molecules. We disclose copper-photoredox-catalyzed using diaryliodonium reagents (DAIRs) as arylating agents. This strategy harnesses underexplored ability DAIRs serve agents under visible-light irradiation copper salts photocatalysts. The method applies glycine-selective C–H peptides with electronically structurally diverse DAIRs. Moreover, we demonstrate photoinduced copper-catalyzed single electron transfer (SET) can be coupled halogen atom (XAT) process presence alkyl iodides accomplish alkylation glycines peptides. In this synergistic SET/XAT approach, phenyl radicals generated from diphenyl iodonium triflate mediate XAT generate iodides. Both these methods operate mild conditions exhibit broad scope appreciable functional group tolerance. Overall, divergent toolbox presented here facilitate access various alkylated arylated enable bioconjugation between drug

Язык: Английский

Процитировано

2
Organophotoredox Catalyzed C‒O Bond Cleavage: A Chemoselective Deprotection Strategy for Phenolic Ethers and Esters Driven by the Oxophilicity of Silicon DOI Creative Commons

Tanumoy Mandal,

Malekul Islam,

Sanat Kumar Mahapatra

и другие.

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

Процитировано

1
Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI Creative Commons
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

и другие.

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

Процитировано

1