Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations

doi:10.6023/cjoc202108032

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (3): 665-678.DOI: 10.6023/cjoc202108032 Previous Articles Next Articles

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亚稳醌类分子的活性调控与仿生催化反应

左鸿华, 钟芳锐^*()

华中科技大学化学与化工学院生物医用与防护材料湖北省工程研究中心生物无机化学与药物湖北省重点实验室武汉 430074

收稿日期:2021-08-18 修回日期:2021-11-02 发布日期:2021-11-09
通讯作者: 钟芳锐

作者简介:

左鸿华, 硕士. 2018年本科毕业于三峡大学生物与制药学院, 同年保送至华中科技大学化学与化工学院攻读硕士学位, 师从钟芳锐教授. 2021年6月获得有机化学专业硕士学位并接受国家留学基金委资助前往德国柏林工业大学Martin Oestreich教授课题组攻读博士学位. 硕士期间主要从事亚稳醌的活性调控与仿生催化反应、有机小分子不对称催化反应研究.

钟芳锐, 博士. 华中科技大学化学与化工学院教授,博士生导师, 入选湖北省海外高层次人才计划. 2008年本科毕业于浙江大学化学系, 2012年获得新加坡国立大学博士学位, 师从知名有机化学家卢一新教授. 2013年至2015年先后在德国慕尼黑工业大学和乌尔姆大学从事博士后研究, 德国洪堡学者(合作导师为德国科学院院士Thorsten Bach教授). 2015年12月起任华中科技大学教授, 主持和参与国家自然科学基金、科技部“合成生物学”重点研究计划、湖北省科技厅技术创新重大专项、深圳市基础研究项目等项目. 目前从事面向可持续化学的绿色催化合成、不对称催化和人工酶催化研究.

基金资助:
国家自然科学基金(21602067)

Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations

Honghua Zuo, Fangrui Zhong()

Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, Hubei Engineering Research Center for Biomaterials and Medical Protective, School of Chemistry and Chemical Engineering, Huazhong University of Science & Technology, Wuhan 430074

Received:2021-08-18 Revised:2021-11-02 Published:2021-11-09
Contact: Fangrui Zhong
Supported by:
National Natural Science Foundation of China(21602067)

Quinones and their imine counterparts constitute a class of highly electrophilic and dearomatized synthon. Their preparation and synthetic applications are challenged by limited stability due to the tendency of dimerization/polymerization and hydrolysis. By taking a biomimetic catalytic oxidation strategy, we have developed oxidation systems comprising metal catalysts and green terminal oxidants that realized in situ oxidation of phenols and reactivity modulation of labile quinone intermediates. This has led to the establishment of several [3+2], [3+3] and [4+2] cycloadditions and control of their regioselectivity and stereoselectivity. In this account, our recent advances in reactivity modulation of labile quinones/quinone imines and their biomimetic catalytic transformations are summarized.

Key words: catalytic oxidation, biomimetic catalysis, relay catalysis, cycloaddition reaction, green synthesis, sustainable chemistry

Cite this article

Honghua Zuo, Fangrui Zhong. Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 665-678.

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Fig. & Tab. 13

Figure 1. General stability of quinones

Figure 2. Direct oxidative in situ generation of labile quinones and their application

Figure 3. PhI(OAc)2 mediated o-phenylenediamines and C=C bond [4+2] oxidative cycloaddition

Figure 4. Biological oxidation of phenolic compounds

Figure 5. Influence of catalyst loading and reaction temperature on the oxidative cycloaddition of 2-aminophenol and enamine

Figure 6. Selected examples of oxidative [4+2] cycloaddition of ortho-aminophenol and enamines

Figure 7. Biomimetic phenol-hydrazone [3+3] oxidative cycloaddition to construct 1,3,4-oxadiazines

Figure 8. Oxidative p-aminophenol-indole [3+2] cycloaddition via relay catalysis to construct benzofuroindolines

Figure 9. Enantioselective phenol-indole [3+2] oxidative cycloaddition enabled by Mn(salen)/CPA relay catalysis

Figure 10. Mechanistic studies on the Mn(salen)/CPA relay catalysis

Figure 11. Assembly of benzofuroindoles via oxidative phenol-indole [3+2] cycloaddition

Figure 12. Cu/Co co-catalyzed phenol-indole oxidative [3+2] reaction and CIE spectrum of 14a

Figure 13. Plausible reaction mechanism of the Cu/Co co-catalyzed phenol-indole [3+2] reaction

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亚稳醌类分子的活性调控与仿生催化反应

Reactivity Modulation of Labile Quinones and Biomimetic Catalytic Transformations

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