Catalytic Selective 1,2-Reduction of Quinolines by Dinuclear Rare Earth Metal Alkyl Complexes

The reactions of RE(CH<sub>2</sub>SiMe<sub>3</sub>)<sub>3</sub>(THF)<sub>2</sub> with <i>N</i>,<i>N</i>-dimethylethyl-functionalized 5,6,7,8-tetrahydroquinolin-8-amino ligand <b>1</b> afforded a series of dinuclear rare earth metal alkyl complexes <b>2a</b>-<b>2d</b> bearing a dianionic 5,6,7,8-tetrahydroquinolin-8-amido ligand through deprotonation and C-H bond activation processes. These dinuclear rare earth metal alkyl complexes efficiently catalyzed the selective 1,2-reduction of quinolines with ammonia borane (H<sub>3</sub>N·BH<sub>3</sub>) to give the corresponding 1,2-dihydroquinolines in high yields, which provided a mild and efficient approach for the synthesis of 1,2-dihydroquinolines with broad functional group compatibility.

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Publication Details

Journal
Organic Letters
Published
2026-01-22
DOI
https://doi.org/10.1021/acs.orglett.5c05201
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Catalytic Selective 1,2-Reduction of Quinolines by Dinuclear Rare Earth Metal Alkyl Complexes

Qingbing Yuan, Donghan Wang, Weiming Sheng, Lijun Zhang et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Catalytic Selective 1,2-Reduction of Quinolines by Dinuclear Rare Earth Metal Alkyl Complexes

Qingbing Yuan, Donghan Wang, Weiming Sheng, Lijun Zhang, Shaowu Wang
article en

Abstract

The reactions of RE(CH<sub>2</sub>SiMe<sub>3</sub>)<sub>3</sub>(THF)<sub>2</sub> with <i>N</i>,<i>N</i>-dimethylethyl-functionalized 5,6,7,8-tetrahydroquinolin-8-amino ligand <b>1</b> afforded a series of dinuclear rare earth metal alkyl complexes <b>2a</b>-<b>2d</b> bearing a dianionic 5,6,7,8-tetrahydroquinolin-8-amido ligand through deprotonation and C-H bond activation processes. These dinuclear rare earth metal alkyl complexes efficiently catalyzed the selective 1,2-reduction of quinolines with ammonia borane (H<sub>3</sub>N·BH<sub>3</sub>) to give the corresponding 1,2-dihydroquinolines in high yields, which provided a mild and efficient approach for the synthesis of 1,2-dihydroquinolines with broad functional group compatibility.

Organic LettersVol. 28(5)
Institute of Molecular Functional Materials (CN), Anhui Normal University (CN), Anhui Polytechnic University (CN)
Openalex Percentile: Top 81%
Catalytic C–H Functionalization Methods
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