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

Wenliang Yan, Xiaoli Ma*, Qifeng Li, Ziyuan Pang, Xiaobo Yang, Yiwen Chen, Zhi Yang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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 oftBuOK by ether solvents is crucial, allowing thetBuO anion to coordinate with the catalyst’s Al center, thus forming a key intermediate.

Original languageEnglish
Pages (from-to)1347-1353
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume23
Issue number6
DOIs
Publication statusPublished - 18 Dec 2024

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Yan, W., Ma, X., Li, Q., Pang, Z., Yang, X., Chen, Y., & Yang, Z. (2024). Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes with aromatic amines. Organic and Biomolecular Chemistry, 23(6), 1347-1353. https://doi.org/10.1039/d4ob01820f