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Visible-Light-Triggered Iodinations Facilitated by Weak Electrostatic Interaction of N-Heterocyclic Carbenes.

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N-heterocyclic carbenes (NHCs) are well-known as ligands and organocatalysts, but there is no recognition for their catalytic role as a stabilizer through electrostatic interaction rather than electron donation. By utilizing… Click to show full abstract

N-heterocyclic carbenes (NHCs) are well-known as ligands and organocatalysts, but there is no recognition for their catalytic role as a stabilizer through electrostatic interaction rather than electron donation. By utilizing the electrostatic interaction, we herein describe the success of a visible-light-triggered radical-radical cross-coupling of N-alkenoxypyridinium salts and NaI, giving a variety of α-iodo ketones. Computational studies characterize the stabilization role of NHCs.

Keywords: heterocyclic carbenes; light triggered; triggered iodinations; visible light; electrostatic interaction; interaction

Journal Title: Organic letters
Year Published: 2020

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