Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes with aromatic amines

Herein, we report a novel Al compound supported by a NacNac ligand that facilitates the anti-Markovnikov hydroamination of aromatic alkenes and primary amines. This represents the first instance of an aluminum-catalyzed intermolecular hydroamination of alkenes, successfully synthesizing a variety of aromatic imine derivatives. The proposed mechanism suggests that the coordination activation of <sup><i>t</i></sup>BuOK by ether solvents is crucial, allowing the <sup><i>t</i></sup>BuO<sup>-</sup> anion to coordinate with the catalyst's Al center, thus forming a key intermediate.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-12-18
DOI
https://doi.org/10.1039/d4ob01820f
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes with aromatic amines

Ziyuan Pang, Xiaobo Yang, Zhi Mao Yang, Xiaoli Ma et al.
5 links
Organic & Biomolecular Chemistry
Catalytic Alkyne Reactions
article

Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes with aromatic amines

Ziyuan Pang, Xiaobo Yang, Zhi Mao Yang, Xiaoli Ma, Qifeng Li, Wenliang Yan, Yiwen Chen
article en

Abstract

Herein, we report a novel Al compound supported by a NacNac ligand that facilitates the anti-Markovnikov hydroamination of aromatic alkenes and primary amines. This represents the first instance of an aluminum-catalyzed intermolecular hydroamination of alkenes, successfully synthesizing a variety of aromatic imine derivatives. The proposed mechanism suggests that the coordination activation of <sup><i>t</i></sup>BuOK by ether solvents is crucial, allowing the <sup><i>t</i></sup>BuO<sup>-</sup> anion to coordinate with the catalyst's Al center, thus forming a key intermediate.

Organic & Biomolecular ChemistryVol. 23(6)
Beijing Institute of Technology (CN)
Openalex Percentile: Top 83%
Catalytic Alkyne Reactions
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