重氮化合物在高分子合成化学中的应用进展★

doi:10.6023/A23050244

化学学报 ›› 2023, Vol. 81 ›› Issue (8): 1015-1029.DOI: 10.6023/A23050244 上一篇下一篇

所属专题：庆祝《化学学报》创刊90周年合辑

综述

重氮化合物在高分子合成化学中的应用进展^★

于乐飞^a, 姚兴奇^a, 王剑波^a^,^b^,^*()

a 北京大学化学与分子工程学院北京分子科学国家研究中心生物有机与分子工程教育部重点实验室北京 100871
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

投稿日期:2023-05-21 发布日期:2023-09-14

作者简介:

于乐飞, 2019年本科毕业于北京大学, 目前在北京大学化学与分子工程学院攻读博士学位(导师: 李子臣教授、王剑波教授). 主要从事基于卡宾以及重氮化合物的高分子聚合反应研究.

姚兴奇, 2017年本科毕业于山东大学, 2022年博士毕业于北京大学化学与分子工程学院(导师: 王剑波教授). 主要从事基于金属卡宾的碳氢键插入与高分子聚合反应研究.

王剑波, 1983年本科毕业于南京理工大学; 1990年获日本北海道大学博士学位; 1990年至1993年在瑞士日内瓦大学从事博士后研究; 1993年至1995年在美国威斯康星大学从事博士后研究; 1995年至今在北京大学化学与分子工程学院开展独立研究工作. 主要从事过渡金属催化的卡宾转移、卡宾偶联以及基于卡宾的高分子聚合等研究.

^★庆祝《化学学报》创刊90周年.

基金资助:
项目受北京分子科学国家研究中心(8202200300)

Recent Advance of Diazo Compounds in Polymer Synthesis^★

Lefei Yu^a, Xing-Qi Yao^a, Jianbo Wang^a^,^b()

a Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2023-05-21 Published:2023-09-14
Contact: *E-mail: wangjb@pku.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
Beijing National Laboratory of Molecular Sciences(8202200300)

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摘要/Abstract

重氮化合物的转化反应在有机合成中已经得到深入的发展, 人们基于此希望将其应用范围进一步延伸至高分子合成化学. 将重氮化合物的高效有机反应发展成高分子聚合方法, 对于实现结构新颖且具有应用价值的聚合物的合成具有重要的意义. 目前, 这一领域仍存在较大的发展空间, 本综述将对近年来重氮化合物在高分子合成化学中应用进行总结, 包括链式聚合、逐步聚合、聚合物末端官能化和聚合物后修饰等四个方面, 最后对重氮化合物在高分子合成领域所存在的挑战进行展望.

关键词: 重氮化合物, 卡宾聚合, 交叉偶联, 末端官能化, 聚合物后修饰

Based on the well development of diazo compound transformations in organic synthesis, it is expected to extend its applications to the field of polymer synthesis. It is of vital importance to transform efficient organic reactions of diazo compounds into new polymerization methodology in order to afford polymers with new structures and functions. Currently, there is still great development potential in the application of diazo compounds in polymer synthesis. This review highlights the recent advancements of polymer synthesis chemistry with diazo compounds, including chain-growth polymerization, step-growth polymerization, end-group functionalization and post-polymerization modification. Transition-metal-catalyzed chain-growth polymerization of diazoacetates constructs C—C main chain from one carbon unit. Through the development of catalytic diazoacetate polymerization, the synthesis of high molecular weight polymers, stereocontrol polymerization and living/controlled polymerization can be realized successively. The stepwise polymerization of diazo compounds originated from their efficient organic conversions. The insertion reaction of diazo compounds into O—H and N—H bonds can be extended to stepwise polymerization to afford polyethers, polyesters and polyamines that are not easily accessible through other synthetic methods, while cross-coupling polymerization of diazo compounds via metal carbene insertion-migration mechanism can realize the synthesis of polymers with novel structures. Diazoacetates and diazomalonates can be employed to regulate the terminal structures of polymers synthesized through metal-catalyzed vinyl addition polymerization or ring-opening metathesis polymerization of olefins, and successively end-capped by metal carbene. The post-polymerization modifications based on diazo compounds can be applied to the introduction of polar functional groups into polyolefin. Compared to the copolymerization of polar olefins, the post-polymerization functionalization strategy avoids the depressed reactivity of varied monomers, and can be applicable to a broad scope of functional groups. The thermal and mechanical properties of polymers can be improved by this method. Finally, the future challenges in expanding the approaches on polymer chemistry of diazo compounds are prospected in this review.

Key words: diazo compound, carbene polymerization, cross coupling, end group functionalization, post modification

引用此文

于乐飞, 姚兴奇, 王剑波. 重氮化合物在高分子合成化学中的应用进展^★[J]. 化学学报, 2023, 81(8): 1015-1029.

Lefei Yu, Xing-Qi Yao, Jianbo Wang. Recent Advance of Diazo Compounds in Polymer Synthesis^★[J]. Acta Chimica Sinica, 2023, 81(8): 1015-1029.

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图/表 39

图1. C2聚合与C1聚合反应对比

Figure 1. Comparison between C2 and C1 polymerization

图2. 首例过渡金属催化的重氮乙酸酯的链式聚合

Figure 2. First transition-metal-catalyzed chain-growth polymerization of diazoacetates

图3. Pd催化卡宾聚合反应的机理

Figure 3. Proposed mechanism for Pd-catalyzed polymerization of carbene

图4. (NHC)Pd配合物催化重氮乙酸酯的链式聚合

Figure 4. Polymerization of diazoacetates catalyzed by (NHC)Pd complexes

图5. [(π-allyl)PdCl]2催化重氮乙酸酯的链式聚合

Figure 5. Polymerization of diazoacetates catalyzed by [(π-allyl)PdCl]2

图6. Pd(nq)2/NaBPh4催化重氮乙酸酯的链式聚合

Figure 6. Polymerization of diazoacetates catalyzed by Pd(nq)2/NaBPh4

图7. 环戊二烯烯丙基钯催化重氮乙酸酯的链式聚合

Figure 7. Polymerization of diazoacetates catalyzed by Cp(π-allyl)Pd

图8. 双(N-芳基马来酰亚胺)钯/NaBPh4催化重氮乙酸酯的链式聚合

Figure 8. Polymerization of diazoacetates catalyzed by Pd(N-aryl- maleimide)/NaBPh4

图9. 含有环状磷腈基团的重氮乙酸酯的活性聚合

Figure 9. Living polymerization of diazoacetates containing cyclophosphazene group

图10. (π-allyl)PdCl/Wei-Phos催化重氮乙酸酯的活性/可控聚合

Figure 10. Living/controlled polymerization of diazoacetates catalyzed by (π-allyl)PdCl/Wei-Phos

图11. 三氟重氮乙烷的活性/可控C1聚合

Figure 11. Living polymerization of 2-diazo-1,1,1-trifluoroethane

图12. [(π-allyl)PdOAc]2催化重氮乙酸酯的准活性聚合

Figure 12. Quasi-living polymerization of diazoacetates catalyzed by [(π-allyl)PdOAc]2

图13. 铑催化重氮乙酸酯的链式聚合

Figure 13. Rh-mediated chain-growth polymerization of diazoacetates

图14. 铑催化重氮乙酸酯的链式聚合的反应机理

Figure 14. Mechanism of Rh-mediated polymerization of diazoacetates

图15. [(allyl)RhIII-OH]+引发重氮乙酸酯的链式聚合的反应机理

Figure 15. Mechanism of diazoacetate polymerization initiated by [(allyl)RhIII-OH]+

图16. 醇类控制链转移的反应机理

Figure 16. Mechanism of alcohol-mediated chain-transfer

图17. 阳离子[(cycloocta-2,6-dien-1-yl)Rh(III)(alkyl)]+催化的卡宾聚合

Figure 17. Carbene polymerization catalyzed by [(cycloocta-2,6-dien-1-yl)Rh(III)(alkyl)]+

图18. 重氮乙酸酯与硫叶立德的共聚反应

Figure 18. Copolymerization of diazoacetates and sulfoxonium ylides

图19. Ni催化重氮乙酸酯的活性/可控聚合

Figure 19. Nickel-catalyzed living/controlled polymerization of diazoacetates

图20. BF3催化重氮化合物的活性/可控聚合

Figure 20. Living/controlled polymerization of diazo compounds catalyzed by BF3

图21. Carothers方程

Figure 21. Carothers equation

图22. 重氮化合物与二酚或二酸的逐步聚合反应

Figure 22. Stepwise polymerization between diazo compounds and biphenol or dicarboxylic acid

图23. 双-α-重氮酯与二胺的逐步聚合反应

Figure 23. Stepwise polymerization of bis-α-diazoesters and diamines

图24. 双-α-重氮酯与硅烷的对映选择性逐步聚合反应

Figure 24. Enantioselective stepwise polymerization between bis-α- diazoesters and silanes

图25. 双重氮化合物的二聚聚合反应

Figure 25. Dimerize polymerization of bis-diazo compounds

图26. 基于金属卡宾交叉偶联反应的逐步聚合

Figure 26. Stepwise polymerization based on cross-coupling reaction of metal carbene

图27. 交叉偶联聚合反应合成聚亚芳基乙烯撑

Figure 27. Synthesis of PAVs through cross-coupling polymerization

图28. 交叉偶联聚合反应合成轴手性联烯聚合物

Figure 28. Synthesis of polyallenoates with axial chirality through cross-coupling polymerization

图29. 双-α-重氮酯与双烯丙基硫醚的逐步聚合反应

Figure 29. Stepwise polymerization of bis-α-diazoesters and bis(allyl sulfides)

图30. 三组分Hooz逐步聚合反应合成聚-β-羟基酮

Figure 30. Synthesis of poly(β-hydroxyketone)s through three- component Hooz stepwise polymerization

图31. 重氮丙二酸酯对乙烯配位聚合的封端反应

Figure 31. End-capping reaction of diazo malonate for coordination polymerization of ethylene

图32. 重氮化合物与环辛烯的聚合反应

Figure 32. Polymerization of diazo compounds and cyclooctene

图33. 重氮乙酸酯对降冰片烯开环易位聚合的封端反应

Figure 33. End-capping reaction of diazoacetates for ring-opening metathesis polymerization of norbornene

图34. 侧链含有重氮基团的聚合物的C—H键插入后修饰反应

Figure 34. Post-polymerization modification of polymers with diazo group on side chain through C—H insertion

图35. 铜催化下重氮乙酸乙酯修饰聚烯烃

Figure 35. Copper-mediated post modification of polyolefins by ethyl diazoacetate

图36. 双吖丙啶对聚合物主链的修饰反应

Figure 36. Post modification of polymers by bis-diazirine

图37. 双吖丙啶交联试剂的发展

Figure 37. Development of bis-diazirine crosslinkers

图38. 双吖丙啶动态交联试剂

Figure 38. Dynamic bis-diazirine crosslinkers

图39. 重氮交联试剂的结构设计和优化

Figure 39. Design and optimization of diazo crosslinkers

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重氮化合物在高分子合成化学中的应用进展^★

Recent Advance of Diazo Compounds in Polymer Synthesis^★

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重氮化合物在高分子合成化学中的应用进展★

Recent Advance of Diazo Compounds in Polymer Synthesis★

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重氮化合物在高分子合成化学中的应用进展^★

Recent Advance of Diazo Compounds in Polymer Synthesis^★