Ligand-PromotedRemote γ‑C(sp<sup>3</sup>)–H Chlorination andBromination of Alcohols

Herein, we report a Pd(II)-catalyzed protocol f-C(sp<sup>3</sup>)–H chlorination and bromination of aliphatic alcohols using NCS and NBS as the halogenating reagents. The addition of 2-pyridone ligand and base was crucial to the success of the reaction. The method showed excellent functional group tolerance. The gram-scale reaction and the facile removal of the directing group demonstrated its potential application in the synthesis of γ-chloro or bromo alcohols containing quaternary carbon.

Publication Details

Journal
Figshare
Published
2025-02-04
DOI
https://doi.org/10.1021/acs.joc.4c03031.s001
Primary Topic
Catalytic C–H Functionalization Methods
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article
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Ligand-PromotedRemote γ‑C(sp3)–H Chlorination andBromination of Alcohols

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Catalytic C–H Functionalization Methods
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Ligand-PromotedRemote γ‑C(sp3)–H Chlorination andBromination of Alcohols

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Abstract

Herein, we report a Pd(II)-catalyzed protocol f-C(sp<sup>3</sup>)–H chlorination and bromination of aliphatic alcohols using NCS and NBS as the halogenating reagents. The addition of 2-pyridone ligand and base was crucial to the success of the reaction. The method showed excellent functional group tolerance. The gram-scale reaction and the facile removal of the directing group demonstrated its potential application in the synthesis of γ-chloro or bromo alcohols containing quaternary carbon.

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Catalytic C–H Functionalization Methods
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Ligand-PromotedRemote γ‑C(sp<sup>3</sup>)–H Chlorination andBromination of Alcohols · Figshare (2025) | TGRS Research Map | TGRS