Ni(<scp>ii</scp>)-catalyzed nucleophilic substitution for the synthesis of allenylselenide

A method for synthesizing allenylselenides has been developed using readily available propargyl carbonate and phenylselenol. The reaction is catalyzed by Ni(II) and proceeds <i>via</i> a migratory insertion and β-oxygen elimination mechanism. Due to the strong interaction between Se and Ni leading to catalyst deactivation, zinc salt was used to mitigate the deleterious effects of Se anions on the catalyst, thereby facilitating the successful synthesis of the target products.

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Publication Details

Journal
Chemical Communications
Published
2024-12-11
DOI
https://doi.org/10.1039/d4cc05065g
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
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article

Ni(ii)-catalyzed nucleophilic substitution for the synthesis of allenylselenide

Ling-Hong Zeng, Zhuo Huang, Ranran Cui, Qing‐Wei Zhang
Chemical Communications
Catalytic Alkyne Reactions
article

Ni(ii)-catalyzed nucleophilic substitution for the synthesis of allenylselenide

Ling-Hong Zeng, Zhuo Huang, Ranran Cui, Qing‐Wei Zhang
article en

Abstract

A method for synthesizing allenylselenides has been developed using readily available propargyl carbonate and phenylselenol. The reaction is catalyzed by Ni(II) and proceeds <i>via</i> a migratory insertion and β-oxygen elimination mechanism. Due to the strong interaction between Se and Ni leading to catalyst deactivation, zinc salt was used to mitigate the deleterious effects of Se anions on the catalyst, thereby facilitating the successful synthesis of the target products.

Chemical CommunicationsVol. 61(6)
University of Science and Technology of China (CN)
Openalex Percentile: Top 83%
Catalytic Alkyne Reactions
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