Exogenous photocatalyst-free aryl radical generation from diaryliodonium salts and use in metal-catalyzed C–H arylation

Galicia, Jonathan; McDonald, Nicholas R.; Bennett, Christopher W.; He, Jiajun; Glossbrenner, Mark D.; Romero, Erik A.

doi:10.1039/d4cc01259c

Chem. Commun.

2024

DOI: 10.1039/d4cc01259c

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Exogenous photocatalyst-free aryl radical generation from diaryliodonium salts and use in metal-catalyzed C–H arylation

Jonathan Galicia,

Nicholas R. McDonald,

Christopher W. Bennett

et al.

Abstract: 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 by transition-metals for...

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2024

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Cited by 2 publications

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Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts

Bennett,

McDonald,

Siddiqui

et al. 2024

ChemPhotoChem

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Direct functionalization of C–H bonds is the most expeditious strategy to build complexity into organic molecules. Unfortunately, most Pd‐catalyzed C–H arylation strategies require high temperatures and/or stoichiometric oxidants. The discovery of metallaphotoredox C–H arylation in 2011 forged a new approach to achieve metal catalyzed C–H arylation at room temperature. Since this discovery, most reports still use explosive diazonium salts as aryl radical precursors. Alternatively, a single report uses bench‐stable diaryliodonium salts, albeit with an Ir‐based photocatalyst. In this study, we develop an organophotoredox manifold that enables Pd‐catalyzed C–H arylation of numerous N‐aryl amide substrates. The results we present are expected to revitalize the use of diaryliodonium salts to achieve room temperature arylations of wide‐ranging classes of C–H bonds.

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Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts

Bennett,

McDonald,

Siddiqui

et al. 2024

ChemPhotoChem

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Novel electron donor–acceptor (EDA) complex promoted arylation of 2-oxo-2H-chromene-3-carbonitriles under visible light irradiation

Sahoo,

Prasanna,

Sridhar

et al. 2024

Org. Biomol. Chem.

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Exogenous photocatalyst-free aryl radical generation from diaryliodonium salts and use in metal-catalyzed C–H arylation

Abstract: 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 by transition-metals for...

Cited by 2 publications

References 55 publications

Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts

Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts

Novel electron donor–acceptor (EDA) complex promoted arylation of 2-oxo-2H-chromene-3-carbonitriles under visible light irradiation

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