Transition-Metal-Catalyzed Polymerization of Cyclopropenes

doi:10.6023/cjoc202010024

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 1888-1896.DOI: 10.6023/cjoc202010024 Previous Articles Next Articles

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过渡金属催化的环丙烯聚合反应研究

张泽鹏^a^,^b, 郜云鹏^a, 陈树峰^b^,^*(), 王剑波^a^,^*()

a 北京大学化学与分子工程学院生物有机与分子工程教育部重点实验室北京分子科学国家中心北京 100871
b 内蒙古大学化学化工学院内蒙古自治区精细有机合成重点实验室呼和浩特 010021

收稿日期:2020-10-16 修回日期:2020-11-08 发布日期:2020-12-01
通讯作者: 陈树峰, 王剑波
基金资助:
国家自然科学基金(91956104); 北京市高等学校卓越青年科学家计划(BJJWZYJH01201910001001)

Transition-Metal-Catalyzed Polymerization of Cyclopropenes

Zepeng Zhang^a^,^b, Yunpeng Gao^a, Shufeng Chen^b^,^*(), Jianbo Wang^a^,^*()

a Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871
b Inner Mongolia Key Laboratory of Fine Organic Synthesis, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021

Received:2020-10-16 Revised:2020-11-08 Published:2020-12-01
Contact: Shufeng Chen, Jianbo Wang
About author:
* Corresponding authors. E-mail: wangjb@pku.edu.cn;
E-mail: shufengchen@imu.edu.cn
Supported by:
National Natural Science Foundation of China(91956104); Beijing Outstanding Young Scientist Program(BJJWZYJH01201910001001)

As the smallest unsaturated cyclic compounds in nature, cyclopropenes serve as important synthetic intermediates in organic chemistry as well as unique monomers in polymerization. While cyclopropenes are mostly explored in the domain of organic chemistry, the polymerization reaction of cyclopropenes has gradually attracted the attentions of chemists in recent years. The research progress of cyclopropene polymerization is reviewed, including addition polymerization and ring-opening metathesis polymerization (ROMP), and prospects for the future development of this field from the perspective of polymer synthesis methodolody.

Key words: cyclopropene, transition-metal catalysis, addition polymerization, ring-opening metathesis polymerization

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Zepeng Zhang, Yunpeng Gao, Shufeng Chen, Jianbo Wang. Transition-Metal-Catalyzed Polymerization of Cyclopropenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1888-1896.

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Fig. & Tab. 18

Scheme 1. Polymerization of cyclopropenes (CPEs)

Scheme 2. Formation of dimer and oligomers with palladium complexes

Scheme 3. Palladium-catalyzed addition polymerization of CPEs

Scheme 4. Rhodium-catalyzed polymerization via 1,4-rhodium migration

Scheme 5. ROMP of CPEs and its general mechanism

Scheme 6. Mo-catalyzed ROMP of CPEs

Scheme 7. Control of tacticity in Mo-catalyzed ROMP of CPEs

Scheme 8. Proposed mechanism of Mo-catalyzed ROMP of CPEs

Scheme 9. ROMP of 4 and block copolymerization using Grubbs catalysts

Scheme 10. Z-selective ROMP of CPE 4

Scheme 11. Z-selective ROMP of CPE 10

Scheme 12. Controlled ROMP of 12a~12h using the 3rd Grubbs catalyst

Scheme 13. Controlled ROMP of 13 using the 3rd Grubbs catalyst

Scheme 14. End-capping for ROMP using CPE 13

Scheme 15. Synthesis of degradable polymers using AROMP

Scheme 16. Precise placement of CPE and NBE in ROMP

Scheme 17. Effect of the structure on the reactivity

Scheme 18. Comparison of polymerization patterns of different CPEs

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过渡金属催化的环丙烯聚合反应研究

Transition-Metal-Catalyzed Polymerization of Cyclopropenes

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