Photoinduced Vitamin‑B<sub>12</sub>-Catalyzed <i>meta</i>-C–H Bromination/Chlorination of Phenol Derivatives\nAssisted by a U‑Shaped Nitrile Template

A photoinduced\nvitamin-B<sub>12</sub>-catalyzed <i>meta</i>-C–H\nbromination/chlorination of phenol derivatives was established\nusing a nitrile directing template and <i>N</i>-bromosuccinimide\n(NBS)/<i>N</i>-chlorosuccinimide (NCS) as halogenated reagents,\nand a series of <i>meta</i>-bromination/chlorination products\nwere obtained in yields of 51 to 80%. This strategy overcame the selectivity\nproblem of phenols, which have difficulty obtaining <i>meta</i>-products through conventional electrophilic reactions. Furthermore,\nnatural product resveratrol and an intermediate of the γ-secretase\ninhibitor were successfully synthesized, which demonstrates the practicability\nof this method.

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Publication Details

Journal
Figshare
Published
2024-10-15
DOI
https://doi.org/10.1021/acs.orglett.4c03339.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

Photoinduced Vitamin‑B12-Catalyzed meta-C–H Bromination/Chlorination of Phenol Derivatives\nAssisted by a U‑Shaped Nitrile Template

Figshare
Catalytic C–H Functionalization Methods
article

Photoinduced Vitamin‑B12-Catalyzed meta-C–H Bromination/Chlorination of Phenol Derivatives\nAssisted by a U‑Shaped Nitrile Template

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Abstract

A photoinduced\nvitamin-B<sub>12</sub>-catalyzed <i>meta</i>-C–H\nbromination/chlorination of phenol derivatives was established\nusing a nitrile directing template and <i>N</i>-bromosuccinimide\n(NBS)/<i>N</i>-chlorosuccinimide (NCS) as halogenated reagents,\nand a series of <i>meta</i>-bromination/chlorination products\nwere obtained in yields of 51 to 80%. This strategy overcame the selectivity\nproblem of phenols, which have difficulty obtaining <i>meta</i>-products through conventional electrophilic reactions. Furthermore,\nnatural product resveratrol and an intermediate of the γ-secretase\ninhibitor were successfully synthesized, which demonstrates the practicability\nof this method.

Figshare
Heilongjiang University (CN)
Openalex Percentile: Top 60%
Catalytic C–H Functionalization Methods
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