Palladium Catalyzed Cyanation of Diaryl Sulfoxides

Aryl nitriles are highly versatile and useful compounds. A palladium-catalyzed cyanation of diaryl sulfoxides using bench-stable Zn(CN)<sub>2</sub> as the cyanating reagent has been developed. The reaction proceeded well using Pd(OAc)<sub>2</sub> as the catalyst with the inexpensive ligand PCy<sub>3</sub> in the presence of <i>t</i>-BuONa. The method has a broad scope of substrates and is scalable. The regioselective cyanation of unsymmetrical diaryl sulfoxides was observed at the side of electron-deficient and more steric hindered aryl groups.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-07
DOI
https://doi.org/10.1021/acs.joc.4c02506
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.25

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article

Palladium Catalyzed Cyanation of Diaryl Sulfoxides

Xianchao Qiu, Benqiang Cui, Yanhui Shi, Changsheng Cao et al.
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The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
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article

Palladium Catalyzed Cyanation of Diaryl Sulfoxides

Xianchao Qiu, Benqiang Cui, Yanhui Shi, Changsheng Cao, Guangcai Qu
article en
1 citations

Abstract

Aryl nitriles are highly versatile and useful compounds. A palladium-catalyzed cyanation of diaryl sulfoxides using bench-stable Zn(CN)<sub>2</sub> as the cyanating reagent has been developed. The reaction proceeded well using Pd(OAc)<sub>2</sub> as the catalyst with the inexpensive ligand PCy<sub>3</sub> in the presence of <i>t</i>-BuONa. The method has a broad scope of substrates and is scalable. The regioselective cyanation of unsymmetrical diaryl sulfoxides was observed at the side of electron-deficient and more steric hindered aryl groups.

The Journal of Organic ChemistryVol. 89(23)
Jiangsu Normal University (CN)
National Natural Science Foundation of China, Jiangsu Normal University
Clean water and sanitation
Openalex Percentile: Top 47%
Catalytic C–H Functionalization Methods
0.25
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