Synthesis of Phosphangulene-Derived Chiral Monophosphorus Ligands

doi:10.6023/cjoc202510033

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (5): 2149-2155.DOI: 10.6023/cjoc202510033 Previous Articles Next Articles

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基于膦杂碗烯的螺旋手性单膦配体合成

王明慧^†, 刘祖恋^†, 杨德玺, 苏嘉琪, 徐嘉麒, 付海燕, 李瑞祥, 陈华, 郑学丽^*(), 薛卫超^*()

四川大学化学学院成都 610064

收稿日期:2025-10-30 修回日期:2025-12-12 发布日期:2026-01-23
作者简介:
†共同第一作者
基金资助:
四川省科技厅自然科学基金(2024YFFK0016); 四川省科技厅自然科学基金(2024ZYD0099); 中央高校基本科研业务费(20822041J4097); 中央高校基本科研业务费(0082604151502)

Synthesis of Phosphangulene-Derived Chiral Monophosphorus Ligands

Minghui Wang, Zulian Liu, Dexi Yang, Jiaqi Su, Jiaqi Xu, Haiyan Fu, Ruixiang Li, Hua Chen, Xueli Zheng^*(), Weichao Xue^*()

College of Chemistry, Sichuan University, Chengdu 610064

Received:2025-10-30 Revised:2025-12-12 Published:2026-01-23
Contact: * E-mail: zhengxueli@scu.edu.cn; weichaoxue@scu.edu.cn
About author:
These authors contributed equally to this work
Supported by:
Sichuan Provincial Natural Science Foundation(2024YFFK0016); Sichuan Provincial Natural Science Foundation(2024ZYD0099); Fundamental Research Funds for the Central Universities(20822041J4097); Fundamental Research Funds for the Central Universities(0082604151502)

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Abstract

The development of novel chiral phosphine ligands is a key area of research in organic synthesis. An efficient synthetic method for the preparation of helically chiral monophosphorus ligands was reported. Using this approach, four structurally distinct, helically chiral, bowl-shaped monophosphorus ligands were successfully synthesized. Their catalytic activities were systematically evaluated in palladium-catalyzed C—C and C—N bond-forming reactions. Enantiopure ligands were obtained via HPLC resolution. Although these reactions did not achieve high enantiocontrol, the ligands demonstrated a unique helical chiral cavity and excellent catalytic activity. These findings suggest that this class of compounds warrants further exploration in other asymmetric catalytic reactions.

Key words: phosphorus ligand, helically chiral, bowl shape, catalysis

Cite this article

Minghui Wang, Zulian Liu, Dexi Yang, Jiaqi Su, Jiaqi Xu, Haiyan Fu, Ruixiang Li, Hua Chen, Xueli Zheng, Weichao Xue. Synthesis of Phosphangulene-Derived Chiral Monophosphorus Ligands[J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 2149-2155.

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Fig. & Tab. 5

Figure 1. (a) Selected examples of chiral phosphorus ligands and (b) the helically chiral ligands developed in this work

Scheme 1. Synthesis of helically chiral ligand

Figure 2. Crystal structure of 6a

Scheme 2. Investigation of ligand activity in C—C and C—N bond formation

Figure 3. (a) UV spectra of ligands 7 and (b) CD spectra of ligand 7d

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基于膦杂碗烯的螺旋手性单膦配体合成

Synthesis of Phosphangulene-Derived Chiral Monophosphorus Ligands

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