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Borenium-ion-catalyzed hydrogenation of arenes
Yizhou Yang1, Yuliang Xu1, Huadong Wang1
1Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Songhu Road 2005, Shanghai, 200438, China. huadongwang@fudan.edu.cn.
Abstract:
Non-metal-catalyzed hydrogenation of arenes represents a sustainable and environment-friendly approach for the synthesis of cyclohexane derivatives. Herein, we report the development of a borenium-ion catalyst system which can hydrogenate a number of monocyclic arenes. Additionally, this metal-free catalytic system allows selective partial or full hydrogenation of naphthalene and anthracene by modification of the reaction conditions. Our mechanism studies suggest that the borenium-arene-mediated H2 splitting takes place before the rate-limiting step and the hydride transfer between the resulting neutral borane and protonated arene is likely the rate-limiting step in the catalytic process.
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