Copper(II)‐Catalyzed Regioselective H/D Exchange Based on Reversible C−H Activation

Despite the increasing use of copper in C-H functionalizations, the Cu-catalyzed direct deuteration of C-H bonds remains a significant challenge due to its inherent low reactivity in inverse C-H bond reconstruction. In this paper, a novel strategy had been developed to reverse the copper-catalyzed concerted metalation-deprotonation process by inhibiting the unexpected disproportionation of Cu(II) to Cu(III). Picolinic acid was identified as a powerful ligand for facilitating this H/D exchange with D<sub>2</sub>O as deuterium source, and its inhibition activity was supported by preliminary control experiments and DFT studies.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-10-17
DOI
https://doi.org/10.1002/chem.202403121
Citations
4
Primary Topic
Chemical Reactions and Isotopes
Type
article
Field-Weighted Citation Impact
0.83

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article

Copper(II)‐Catalyzed Regioselective H/D Exchange Based on Reversible C−H Activation

Lijie Duan, Jian‐Fei Bai, Zhanghua Gao, Zhi‐Jiang Jiang et al.
4 citations
Chemistry - A European Journal
Chemical Reactions and Isotopes
0.83
article

Copper(II)‐Catalyzed Regioselective H/D Exchange Based on Reversible C−H Activation

Lijie Duan, Jian‐Fei Bai, Zhanghua Gao, Zhi‐Jiang Jiang, Jia Chen, Jiawei Han, Yuhang Su
article en
4 citations

Abstract

Despite the increasing use of copper in C-H functionalizations, the Cu-catalyzed direct deuteration of C-H bonds remains a significant challenge due to its inherent low reactivity in inverse C-H bond reconstruction. In this paper, a novel strategy had been developed to reverse the copper-catalyzed concerted metalation-deprotonation process by inhibiting the unexpected disproportionation of Cu(II) to Cu(III). Picolinic acid was identified as a powerful ligand for facilitating this H/D exchange with D<sub>2</sub>O as deuterium source, and its inhibition activity was supported by preliminary control experiments and DFT studies.

Chemistry - A European JournalVol. 30(72)
Ningbo University of Technology (CN), Zhejiang University (CN)
National Natural Science Foundation of China, Ningbo Municipal Bureau of Science and Technology, Natural Science Foundation of Ningbo
Clean water and sanitation
Openalex Percentile: Top 31%
Chemical Reactions and Isotopes
0.83
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Copper(II)‐Catalyzed Regioselective H/D Exchange Based on Reversible C−H Activation — Lijie Duan, Jian‐Fei Bai, et al. · Chemistry - A European Journal (2024) | TGRS Research Map | TGRS