Nickel-Catalyzed Desulfurative Cross-Coupling of Aryl Iodides with Heteroaromatic Thioethers via C–S Bond Cleavage

Herein, we present a Ni-catalyzed direct cross-coupling of heteroaromatic thioethers with aryl iodides via selective C(sp<sup>2</sup>)-S bond cleavage under reductive conditions, thereby providing various biaryl frameworks with high efficiency. Mechanistic studies suggested Mo(CO)<sub>6</sub> played a crucial role in facilitating the activation of the C(sp<sup>2</sup>)-S bond. This protocol demonstrated a wide substrate scope, operational simplicity, and good functional group compatibility. Furthermore, the utility of this reaction was highlighted by facile scale-up and sequential modification of heteroaryl frameworks.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-15
DOI
https://doi.org/10.1021/acs.joc.4c00678
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.50

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article

Nickel-Catalyzed Desulfurative Cross-Coupling of Aryl Iodides with Heteroaromatic Thioethers via C–S Bond Cleavage

Pingliang Zhu, Xinjin Li, Fenggang Sun, Hui Liu et al.
2 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.50
article

Nickel-Catalyzed Desulfurative Cross-Coupling of Aryl Iodides with Heteroaromatic Thioethers via C–S Bond Cleavage

Pingliang Zhu, Xinjin Li, Fenggang Sun, Hui Liu, Yu Zhao, Baolong Xu, Shaowen Ling
article en
2 citations

Abstract

Herein, we present a Ni-catalyzed direct cross-coupling of heteroaromatic thioethers with aryl iodides via selective C(sp<sup>2</sup>)-S bond cleavage under reductive conditions, thereby providing various biaryl frameworks with high efficiency. Mechanistic studies suggested Mo(CO)<sub>6</sub> played a crucial role in facilitating the activation of the C(sp<sup>2</sup>)-S bond. This protocol demonstrated a wide substrate scope, operational simplicity, and good functional group compatibility. Furthermore, the utility of this reaction was highlighted by facile scale-up and sequential modification of heteroaryl frameworks.

The Journal of Organic ChemistryVol. 89(17)
Shandong University of Technology (CN)
National Natural Science Foundation of China, Natural Science Foundation of Shandong Province
Openalex Percentile: Top 40%
Sulfur-Based Synthesis Techniques
0.50
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