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

Abstract 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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Journal
ChemPhotoChem
Published
2024-10-24
DOI
https://doi.org/10.1002/cptc.202400285
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

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

Christopher Bennett, Nicholas McDonald, Erik A. Romero, Amin A. Siddiqui
ChemPhotoChem
Catalytic C–H Functionalization Methods
article

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

Christopher Bennett, Nicholas McDonald, Erik A. Romero, Amin A. Siddiqui
article en

Abstract

Abstract 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.

ChemPhotoChemVol. 9(2)
University of California San Diego (US)
Openalex Percentile: Top 86%
Catalytic C–H Functionalization Methods
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Organophotoredox Pd‐Catalyzed C−H Arylation at Room Temperature using Diaryliodonium Salts — Christopher Bennett, Nicholas McDonald, et al. · ChemPhotoChem (2024) | TGRS Research Map | TGRS