Calixarene Promoted Transition-Metal-Catalyzed Reactions

doi:10.6023/cjoc202012034

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2188-2201.DOI: 10.6023/cjoc202012034 Previous Articles Next Articles

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杯芳烃促进的过渡金属催化反应

马志艳(), 李云剑, 孙小强, 杨科^*(), 李正义^*()

常州大学石油化工学院江苏省绿色催化材料与技术重点实验室江苏常州 213100

收稿日期:2020-12-22 修回日期:2021-02-04 发布日期:2021-02-26
通讯作者: 杨科, 李正义
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21572026); 国家自然科学基金(21702019); 江苏省研究生科研与实践创新计划(KYCX20_2525); 江苏省先进催化与绿色制造协同创新中心资助项目

Calixarene Promoted Transition-Metal-Catalyzed Reactions

Zhiyan Ma(), Yunjian Li, Xiao-Qiang Sun, Ke Yang(), Zheng-Yi Li()

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213100

Received:2020-12-22 Revised:2021-02-04 Published:2021-02-26
Contact: Ke Yang, Zheng-Yi Li
About author:
(These authors contributed equally to this work).
Supported by:
National Natural Science Foundation of China(21572026); National Natural Science Foundation of China(21702019); Postgraduate Research & Practice Innovation Program of Jiangsu Province(KYCX20_2525); Advanced Catalysis and Green Manufacturing Collaborative Innovation Center of Jiangsu Province.

In recent years, transition metal catalyzed reactions have become one of the most effective methods to construct carbon-carbon bonds and carbon-heteroatom bonds in organic chemistry, and have attracted great research interest among chemists. Calixarene is the third-generation supramolecular host compound after crown ether and cyclodextrin, and its coordination properties have always been a hot spot in supramolecular chemistry. By designing and modifying its phenolic hydroxyl group at the lower edge, the para-position of the benzene ring at the upper edge, and the methylene group connecting the benzene ring unit, calixarene can be used as a transition metal catalyst ligand or assembled with transition metal to form a novel catalyst, both of which can be effectively used to promote the transition metal catalyzed reaction. The research progress of calixarene as a ligand for different transition-metal catalysts and their application in various transition metal catalytic reactions in the past ten years is introduced.

Key words: calixarene, transition-metal catalysis, ligand, organic synthesis

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Zhiyan Ma, Yunjian Li, Xiao-Qiang Sun, Ke Yang, Zheng-Yi Li. Calixarene Promoted Transition-Metal-Catalyzed Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2188-2201.

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Fig. & Tab. 16

Scheme 1. Rhodium-catalyzed asymmetric hydrogenation in the presence of chiral phosphate calix[4]arene

Scheme 2. Phosphate calix[4]arene rhodium complex catalyzed hydrogen amination reaction

Scheme 3. Asymmetric hydroformylation of vinylaromatics catalyzed by rhodium diphosphite calix[4]arene

Scheme 4. Asymmetric hydrogenation of olefins catalyzed by chiral aminophosphine-phosphinate calix[4]arene rhodium complex

Scheme 5. Synthesis of calix[4]arene ligands L10 and L11 and the asymmetric allyl amination catalyzed by palladium catalyst

Scheme 6. Suzuki-Miyaura coupling reaction catalyzed by calix[4]arene-palladium catalyst Cat-4

Scheme 7. Preparation of calix[4]arene carbonyl ligands L13 and L14 and their application in Suzuki-Miyaura coupling reaction

Scheme 8. C—C cross-coupling reaction catalyzed by ternary hybrid calix[4]arene catalyst Cat-5

Scheme 9. Synthesis of calix[4]arene manganese catalyst containing trimethylammonium cation Cat-6 and its application in cyclohexene oxidation

Scheme 10. Synthesis of calix[4]arene manganese catalyst in 1,3-alternating conformation and its application in epoxidation of 6- methoxy-2,2-dimethyl-1,2-dihydronaphthalene

Scheme 11. Synthesis of trimethylammonium cation calix[4]arene copper catalyst Cat-9 and its application in the oxidation polymerization of 2,6-dimethylphenol

Scheme 12. Proposed mechanism of oxidative polymerization of 2,6-dimethylphenol

Scheme 13. Application of trimethylammonium cation calix[4] arene copper catalyst Cat-9 in the oxidation reaction of benzyl alcohol and the preparation of quinoxaline

. Sccheme 14 Copper-catalyzed C—S bond coupling reaction promoted by phenanthroline calix[8] arene ligandL19

Scheme 15. Nickel-catalyzed cross-coupling reaction promoted by diphenylphosphino-calix[4]arene ligand L20 and L21

Scheme 16. Cross-coupling reaction catalyzed by calix[6] arene nickel catalyst

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杯芳烃促进的过渡金属催化反应

Calixarene Promoted Transition-Metal-Catalyzed Reactions

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