Switchable <i>N</i> -Haloethylation and C–H Halogenation of NH-Enaminones with 1,2-Dihaloethanes

The switchable reactions between NH-enaminones and 1,2-dihaloethanes (X = Cl and Br) in the form of N -haloethylation and C–H halogenation have been achieved under different conditions. The reactions in the presence of tetraethylammonium bromide (TEAB) and Cs 2 CO 3 lead to N -haloethylation. Meanwhile, the promotion with tetrabutyl ammonium iodide (TBAI) and Et 3 N under air enables the umpolung C–H halogenation in the α-site.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-07-01
DOI
https://doi.org/10.1021/acs.joc.6c01048
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Switchable N -Haloethylation and C–H Halogenation of NH-Enaminones with 1,2-Dihaloethanes

Changfeng Wan, Weijun Yao, Jie‐Ping Wan, Yunyun Liu et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Switchable N -Haloethylation and C–H Halogenation of NH-Enaminones with 1,2-Dihaloethanes

Changfeng Wan, Weijun Yao, Jie‐Ping Wan, Yunyun Liu, Wanting Liang
article en

Abstract

The switchable reactions between NH-enaminones and 1,2-dihaloethanes (X = Cl and Br) in the form of N -haloethylation and C–H halogenation have been achieved under different conditions. The reactions in the presence of tetraethylammonium bromide (TEAB) and Cs 2 CO 3 lead to N -haloethylation. Meanwhile, the promotion with tetrabutyl ammonium iodide (TBAI) and Et 3 N under air enables the umpolung C–H halogenation in the α-site.

The Journal of Organic Chemistry
Zhejiang Sci-Tech University (CN), Nanjing Forestry University (CN), Jiangxi Normal University (CN)
National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 14%
Catalytic C–H Functionalization Methods
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