Activation and C−C Coupling of Aryl Iodides via Bismuth Photocatalysis

Within the emerging field of bismuth redox catalysis, the catalytic formation of C-C bonds using aryl halides would be highly desirable; yet such a process remains a synthetic challenge. Herein, we present a chemoselective bismuth-photocatalyzed activation and subsequent coupling of (hetero)aryl iodides with pyrrole derivatives to access C(sp<sup>2</sup>)-C(sp<sup>2</sup>) linkages through C-H functionalization. This unique reactivity is the result of the bismuth complex featuring two redox state-dependent interactions with light, which 1) activates the Bi(I) complex for oxidative addition via MLCT, and 2) promotes the homolytic cleavage of aryl Bi(III) intermediates through a LLCT process.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2024-10-22
DOI
https://doi.org/10.1002/anie.202418367
Citations
28
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
7.00

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article

Activation and C−C Coupling of Aryl Iodides via Bismuth Photocatalysis

Paolo Cleto Bruzzese, Mauro Mato, Alexios Stamoulis, Josep Cornellà
28 citations
Angewandte Chemie International Edition
Radical Photochemical Reactions
7.00
article

Activation and C−C Coupling of Aryl Iodides via Bismuth Photocatalysis

Paolo Cleto Bruzzese, Mauro Mato, Alexios Stamoulis, Josep Cornellà
article en
28 citations

Abstract

Within the emerging field of bismuth redox catalysis, the catalytic formation of C-C bonds using aryl halides would be highly desirable; yet such a process remains a synthetic challenge. Herein, we present a chemoselective bismuth-photocatalyzed activation and subsequent coupling of (hetero)aryl iodides with pyrrole derivatives to access C(sp<sup>2</sup>)-C(sp<sup>2</sup>) linkages through C-H functionalization. This unique reactivity is the result of the bismuth complex featuring two redox state-dependent interactions with light, which 1) activates the Bi(I) complex for oxidative addition via MLCT, and 2) promotes the homolytic cleavage of aryl Bi(III) intermediates through a LLCT process.

Angewandte Chemie International EditionVol. 64(5)
Max-Planck-Institut für Kohlenforschung (DE), Max Planck Institute for Chemical Energy Conversion (DE)
European Commission, Deutsche Forschungsgemeinschaft, Max-Planck-Gesellschaft, HORIZON EUROPE Framework Programme, H2020 European Research Council, H2020 Marie Skłodowska-Curie Actions
Clean water and sanitation
Openalex Percentile: Top 2%
Radical Photochemical Reactions
7.00
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