多孔有机膦配体聚合物作为可回收配体用于异吲哚啉酮类化合物的合成

doi:10.6023/cjoc202201043

有机化学 ›› 2022, Vol. 42 ›› Issue (7): 2117-2123.DOI: 10.6023/cjoc202201043 上一篇下一篇

研究论文

多孔有机膦配体聚合物作为可回收配体用于异吲哚啉酮类化合物的合成

庞丽萍, 杨昌杰, 林洪敏, 李心宇, 唐海涛^*(), 潘英明^*()

广西师范大学化学与药学学院药物资源化学与分子工程国家重点实验室广西桂林 541004

收稿日期:2022-01-25 修回日期:2022-03-17 发布日期:2022-08-09
通讯作者: 唐海涛, 潘英明
基金资助:
广西重点研发计划(AB18221005); 国家自然科学基金(22061003); 国家自然科学基金(22161008); 广西省自然科学基金(2021GXNSFFA220005); 广西省自然科学基金(RZ1900005748); 广西省自然科学基金(2021GXNSFBA196041)

Porous Organophosphine Ligand Polymers as Recyclable Ligands for the Synthesis of Isoindolinone Compounds

Liping Pang, Changjie Yang, Hongmin Lin, Xinyu Li, Haitao Tang(), Yingming Pan()

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi 541004

Received:2022-01-25 Revised:2022-03-17 Published:2022-08-09
Contact: Haitao Tang, Yingming Pan
Supported by:
Guangxi Key R&D Program(AB18221005); National Natural Science Foundation of China(22061003); National Natural Science Foundation of China(22161008); Natural Science Foundation of Guangxi Province(2021GXNSFFA220005); Natural Science Foundation of Guangxi Province(RZ1900005748); Natural Science Foundation of Guangxi Province(2021GXNSFBA196041)

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摘要/Abstract

报道了金属钯/多孔有机膦配体(Pd/POL-PPh₃)在非均相条件下用于高效合成异吲哚啉酮类化合物. 与均相条件相比, 该方法具有更高的产率. 同时POL-PPh₃可以循环使用, 降低了反应的成本. 该反应中, POL-PPh₃具有多孔结构, 且反应前后的形貌没有发生明显变化, 其独特的稳定性是POL-PPh₃作为多相配体具有高活性以及可回收的根本原因.

关键词: 异吲哚啉酮, 金属钯/多孔有机磷配体, 可重复使用, 高稳定性

Isoindolinone compounds were efficiently synthesized with Pd-metalated/porous organophosphorus ligand (Pd/ POL-PPh₃) under heterogeneous conditions. Compared with homogeneous conditions, this method has higher yield, at the same time, the POL-PPh₃ can be recycled, which reduces the cost of the reaction. In this reaction, POL-PPh₃ has porous structure without obvious change during the reaction progress of the morphology, and this unique stability is the fundamental reason for the high activity and recyclability of POL-PPh₃ as heterogeneous ligand.

Key words: isoindolinone, Pd/POLs, recyclable, high stability

引用此文

庞丽萍, 杨昌杰, 林洪敏, 李心宇, 唐海涛, 潘英明. 多孔有机膦配体聚合物作为可回收配体用于异吲哚啉酮类化合物的合成[J]. 有机化学, 2022, 42(7): 2117-2123.

Liping Pang, Changjie Yang, Hongmin Lin, Xinyu Li, Haitao Tang, Yingming Pan. Porous Organophosphine Ligand Polymers as Recyclable Ligands for the Synthesis of Isoindolinone Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2117-2123.

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图/表 6

图式1. Pd催化的氮杂环化反应

Scheme 1. Pd catalyzed nitrogen heterocyclization

图式2. Pd/POL-PPh3的合成

Scheme 2. Synthesis of Pd/POL-PPh3

图1. Pd/POL-PPh3的(A)SEM图像、(B) TEM图像和(C)元素分析图

Figure 1. (A) SEM image, (B) TEM image and (C) image of the elemental analysis of the Pd/POL-PPh3

表1. 底物适用范围a

Table 1. Substrates scope

图2. POL-PPh3的重复实验研究

Figure 2. Recycling studies of POL-PPh3

图式3. 可能的反应机制

Scheme 3. Plausible mechanism of the reaction

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多孔有机膦配体聚合物作为可回收配体用于异吲哚啉酮类化合物的合成

Porous Organophosphine Ligand Polymers as Recyclable Ligands for the Synthesis of Isoindolinone Compounds

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