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

doi:10.6023/cjoc202201043

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2117-2123.DOI: 10.6023/cjoc202201043 Previous Articles Next Articles

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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

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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Abstract

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

Cite this article

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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Fig. & Tab. 6

Scheme 1. Pd catalyzed nitrogen heterocyclization

Scheme 2. Synthesis of Pd/POL-PPh3

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

Table 1. Substrates scope

Figure 2. Recycling studies of POL-PPh3

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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Fig. & Tab. 6

References 25

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