Recent Advance of Diazo Compounds in Polymer Synthesis★

doi:10.6023/A23050244

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (8): 1015-1029.DOI: 10.6023/A23050244 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

Review

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)

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

Cite this article

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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Fig. & Tab. 39

Figure 1. Comparison between C2 and C1 polymerization

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

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

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

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

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

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

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

Figure 9. Living polymerization of diazoacetates containing cyclophosphazene group

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

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

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

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

Figure 14. Mechanism of Rh-mediated polymerization of diazoacetates

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

Figure 16. Mechanism of alcohol-mediated chain-transfer

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

Figure 18. Copolymerization of diazoacetates and sulfoxonium ylides

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

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

Figure 21. Carothers equation

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

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

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

Figure 25. Dimerize polymerization of bis-diazo compounds

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

Figure 27. Synthesis of PAVs through cross-coupling polymerization

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

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

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

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

Figure 32. Polymerization of diazo compounds and cyclooctene

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

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

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

Figure 36. Post modification of polymers by bis-diazirine

Figure 37. Development of bis-diazirine crosslinkers

Figure 38. Dynamic bis-diazirine crosslinkers

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^★