Citation: Chengyao Zhao, Jingyuan Liao, Yuxiang Zhu, Yiying Zhang, Lianjie Zhai, Junrong Huang, Hengzhi You. Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles[J]. Chinese Chemical Letters, ;2025, 36(6): 110337. doi: 10.1016/j.cclet.2024.110337 shu

Polystyrene-supported phosphoric-acid catalyzed atroposelective construction of axially chiral N-aryl benzimidazoles

Chengyao Zhao ^{a, 1} ,
Jingyuan Liao ^{a, 1} ,
Yuxiang Zhu ^b ,
Yiying Zhang ^c ,
Lianjie Zhai ^{c, *,} ,
Junrong Huang ^{a, *,} ,
Hengzhi You ^{a, d, *,}

a.
School of science, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, China
b.
School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China
c.
State Key Laboratory of Fluorine & Nitrogen Chemicals, Xi'an Modern Chemistry Research Institute, Xi'an 710069, China
d.
Green Pharmaceutical Engineering Research Center, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, China

trihever0210@126.com

hjunrong@hit.edu.cn

youhengzhi@hit.edu.cn

Received Date: 11 March 2024
Revised Date: 29 July 2024
Accepted Date: 12 August 2024
Available Online: 13 August 2024

Figures(6)

The significance of axial chiral compounds in asymmetric organic catalysis, functional materials, and pharmaceutical useful molecules has encouraged advancements in the atroposelective synthesis of such compounds. Herein, we report the first atroposelective construction of axially chiral N-aryl benzimidazoles catalyzed by a polymer-supported chiral phosphoric acid. A varied library of atropisomers has been synthesized in 30%-96% yield with 58%-98% enantiomeric excess (ee) under a straightforward reaction setup (without the use of molecular sieves). Notably, even after 12 cycles, the immobilized catalyst maintained its reactivity and selectivity (TON > 540).
- Asymmetric catalysis,
- Heterogeneous catalysis,
- Chiral phosphoric acid,
- Atroposelective synthesis,
- N-Aryl benzimidazoles
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