Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction

doi:10.1016/j.cjche.2023.02.013

中国化学工程学报 ›› 2023, Vol. 60 ›› Issue (8): 165-172.DOI: 10.1016/j.cjche.2023.02.013

• Full Length Article • 上一篇下一篇

Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction

Yifan Jiang, Bingqi Xie, Jisong Zhang

State Key Lab of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

收稿日期:2022-11-08 修回日期:2023-02-03 出版日期:2023-08-28 发布日期:2023-10-28
通讯作者: Jisong Zhang,E-mail:jiszhang@tsinghua.edu.cn
基金资助:
We gratefully acknowledge the support of the National Natural Science Foundation of China (20222809, 21978146) and Tsinghua-Foshan Innovation Special Fund (2021THFS0214) in this work.

Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction

Yifan Jiang, Bingqi Xie, Jisong Zhang

State Key Lab of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

Received:2022-11-08 Revised:2023-02-03 Online:2023-08-28 Published:2023-10-28
Contact: Jisong Zhang,E-mail:jiszhang@tsinghua.edu.cn
Supported by:
We gratefully acknowledge the support of the National Natural Science Foundation of China (20222809, 21978146) and Tsinghua-Foshan Innovation Special Fund (2021THFS0214) in this work.

摘要/Abstract

摘要： Suzuki-Miyaura reaction of aryl halides with phenylboronic acid using a heterogeneous palladium catalyst based on activated carbons (AC) was systematically investigated in this work. Two different reaction modes (batch procedure and continuous-flow procedure) were used to study the variations of reaction processing. The heterogeneous catalysts presented excellent reactivity and recyclability for iodobenzene and bromobenzene substrates in batch mode, which can be attributed to stabilization of Pd nanoparticles by the thiol and amino groups on the AC supports. However, significant dehalogenation in the reaction mixture and Pd leaching from the heterogeneous catalysts were observed in continuous-flow mode. This unique phenomenon in continuous-flow mode resulted in a dramatic decline in reaction selectivity and durability of heterogeneous catalysts comparing with that of batch mode. In addition, the heterogeneous Pd catalysts with thiol- and amino-modified AC supports exhibited different reactivity and durability in batch and continuous-flow mode owing to the difference of interaction between Pd species and AC supports.

关键词: Suzuki-Miyaura reaction, Heterogeneous palladium catalysts, Activated carbon, Thiol- and amino-functionalization, Catalyst support, Packed bed

Abstract: Suzuki-Miyaura reaction of aryl halides with phenylboronic acid using a heterogeneous palladium catalyst based on activated carbons (AC) was systematically investigated in this work. Two different reaction modes (batch procedure and continuous-flow procedure) were used to study the variations of reaction processing. The heterogeneous catalysts presented excellent reactivity and recyclability for iodobenzene and bromobenzene substrates in batch mode, which can be attributed to stabilization of Pd nanoparticles by the thiol and amino groups on the AC supports. However, significant dehalogenation in the reaction mixture and Pd leaching from the heterogeneous catalysts were observed in continuous-flow mode. This unique phenomenon in continuous-flow mode resulted in a dramatic decline in reaction selectivity and durability of heterogeneous catalysts comparing with that of batch mode. In addition, the heterogeneous Pd catalysts with thiol- and amino-modified AC supports exhibited different reactivity and durability in batch and continuous-flow mode owing to the difference of interaction between Pd species and AC supports.

Key words: Suzuki-Miyaura reaction, Heterogeneous palladium catalysts, Activated carbon, Thiol- and amino-functionalization, Catalyst support, Packed bed

Yifan Jiang, Bingqi Xie, Jisong Zhang. Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction[J]. 中国化学工程学报, 2023, 60(8): 165-172.

Yifan Jiang, Bingqi Xie, Jisong Zhang. Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction[J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 165-172.

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Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction

Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction

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