基于烯烃碳-氢键活化的碳-碳交叉偶联反应

引用本文: 颜瑞, 陈虎, 赵明. 基于烯烃碳-氢键活化的碳-碳交叉偶联反应[J]. 大学化学, 2024, 39(1): 87-94. doi: 10.3866/PKU.DXHX202306052 shu

Citation: Rui Yan, Hu Chen, Ming Zhao. C—C Cross Coupling Reaction Based on Olefinic C-H Bond Activation[J]. University Chemistry, 2024, 39(1): 87-94. doi: 10.3866/PKU.DXHX202306052 shu

基于烯烃碳-氢键活化的碳-碳交叉偶联反应

颜瑞 ^1,2, ,
陈虎 ^1, ,
赵明 ^{1,
,}

1.
合肥师范学院化学与制药工程学院, 安徽省药食同源天然资源开发与利用工程实验室, 合肥 230601;
2.
中国科学技术大学中国科学院软物质化学重点实验室, 合肥 230026

通讯作者: 赵明,Email:zhaomnwu@126.com

基金项目:
合肥师范学院自然科学重点项目（2021KJZD03，2021KJZD10）；安徽省药食同源天然资源开发与利用工程实验室（YSTY2022022）；安徽省科技重大专项（201903a07020003）；安徽省阜阳市科技重大专项（FK20208018）；安徽省高等学校自然科学研究项目（2022AH052164）；2023年省级大学生创新创业训练计划项目（S202314098083）

摘要: 烯烃是一类非常重要的化合物，人们可以由烯烃通过一系列转化得到复杂的有机分子。本文主要对基于烯烃碳-氢键活化的碳-碳交叉偶联反应进行了详细介绍，基于烯烃的碳-氢键活化，利用铑、钯、钴等过渡金属催化剂，通过碳-碳交叉偶联反应，构建各类碳-碳键。对于烯烃碳-氢键活化反应的介绍，能够丰富和拓展有机化学课程中烯烃的知识点，帮助学生了解有机化学的发展前沿，提高学生学习的积极性和主动性，培养学生的科研素养。

关键词:

English

C—C Cross Coupling Reaction Based on Olefinic C-H Bond Activation

Rui Yan ^1,2, ,
Hu Chen ^1, ,
Ming Zhao ^{1,
,}

1.
Anhui Engineering Laboratory for Medicinal and Food Homologous Natural Resources Exploration, College of Chemistry and Pharmacy Engineering, Hefei Normal University, Hefei 230601, China;
2.
CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

Corresponding author: Ming Zhao, zhaomnwu@126.com

Received Date: 27 June 2023

Abstract: Olefins are a very important class of compounds, which can be transformed to various complex organic molecules through a series of transformations. In this paper, C-C cross coupling reaction based on olefinic C-H bond activation is described in detail. Based on the activation of C-H bonds, C-C bonds are constructed through C-C cross coupling reaction by transition metal catalysts such as Rh, Pd and Co. This introduction of olefinic C-H bond activation can enrich and expand the knowledge of olefins in organic chemistry courses, and it is also helpful for students to understand the forefront of organic chemistry development, stimulate their learning enthusiasm and initiative, and cultivate their scientific research literacy.

Key words:

1. [1]
  邢其毅, 裴伟伟, 徐瑞秋, 裴坚. 基础有机化学(上册). 第4版. 北京: 北京大学出版社, 2016: 341–350.
2. [2]
  Sigman, M. S.; Werner, E. W. Acc. Chem. Res. 2012, 45, 874.Sigman, M. S.; Werner, E. W. Acc. Chem. Res. 2012, 45, 874.
3. [3]
  Colby, D. A.; Bergman, R. G.; Ellman, J. A.; Chem. Rev. 2010, 110, 624. Colby, D. A.; Bergman, R. G.; Ellman, J. A.; Chem. Rev. 2010, 110, 624.
4. [4]
  Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814.
5. [5]
  Gung, B. W.; Kumi, G. J. Org. Chem. 2004, 69, 3488.Gung, B. W.; Kumi, G. J. Org. Chem. 2004, 69, 3488.
6. [6]
  Fontana, A.; d’lppolito, G.; D’Souza, L.; Mollo, E.; Parameswaram, P. S.; Cimino, G. J. Nat. Prod. 2001, 64, 131.Fontana, A.; d’lppolito, G.; D’Souza, L.; Mollo, E.; Parameswaram, P. S.; Cimino, G. J. Nat. Prod. 2001, 64, 131.
7. [7]
  Kong, J. R.; Ngai, M. Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.Kong, J. R.; Ngai, M. Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
8. [8]
  Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F; J. Am. Chem. Soc. 2004, 126, 4130.Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F; J. Am. Chem. Soc. 2004, 126, 4130.
9. [9]
  Finkbeiner, P.; Kloeckner, U.; Nachtsheim, B. J. Angew. Chem. Int. Ed. 2015, 54, 4949.Finkbeiner, P.; Kloeckner, U.; Nachtsheim, B. J. Angew. Chem. Int. Ed. 2015, 54, 4949.
10. [10]
  Caspers, L. D.; Finkbeiner, P.; Nachtsheim, B. J. Chem. Eur. J. 2017, 23, 2748.Caspers, L. D.; Finkbeiner, P.; Nachtsheim, B. J. Chem. Eur. J. 2017, 23, 2748.
11. [11]
  Feng, C.; Feng, D.; Luo, Y.; Loh, T. P. Org. Lett. 2014, 16, 5956.Feng, C.; Feng, D.; Luo, Y.; Loh, T. P. Org. Lett. 2014, 16, 5956.
12. [12]
  Xu, Y.; Zhang, Q.; He, T.; Meng, F.; Loh, T. P. Adv. Synth. Catal. 2014, 356, 1539.Xu, Y.; Zhang, Q.; He, T.; Meng, F.; Loh, T. P. Adv. Synth. Catal. 2014, 356, 1539.
13. [13]
  Negishi, E. Angew. Chem. Int. Ed. 2011, 50, 6738.Negishi, E. Angew. Chem. Int. Ed. 2011, 50, 6738.
14. [14]
  Kuttruff, C. A.; Geiger, S.; Cakmak, M.; Mayer, P.; Trauner, D. Org. Lett. 2012, 14, 1070.Kuttruff, C. A.; Geiger, S.; Cakmak, M.; Mayer, P.; Trauner, D. Org. Lett. 2012, 14, 1070.
15. [15]
  Hubert, P.; Seibel, E.; Beemelmanns, C.; Campagne, J.-M.; Figueiredo, R. M. Adv. Synth. Catal. 2020, 362, 5532.Hubert, P.; Seibel, E.; Beemelmanns, C.; Campagne, J.-M.; Figueiredo, R. M. Adv. Synth. Catal. 2020, 362, 5532.
16. [16]
  Soengas, R. G.; Rodríguez-Solla, H. Molecules 2021, 26, 249.Soengas, R. G.; Rodríguez-Solla, H. Molecules 2021, 26, 249.
17. [17]
  Wen, Z.-K.; Xu, Y.-H.; Loh, T.-P. Chem. Sci. 2013, 4, 4520.Wen, Z.-K.; Xu, Y.-H.; Loh, T.-P. Chem. Sci. 2013, 4, 4520.
18. [18]
  Zhong, X.-M.; Cheng, G.-J.; Chen, P.; Zhang, X.; Wu, Y.-D. Org. Lett. 2016, 18, 5240.Zhong, X.-M.; Cheng, G.-J.; Chen, P.; Zhang, X.; Wu, Y.-D. Org. Lett. 2016, 18, 5240.
19. [19]
  Zhang, X.; Wang, M.; Zhang, M.-X.; Xu, Y.-H.; Loh, T.-P. Org. Lett. 2013, 15, 5531.Zhang, X.; Wang, M.; Zhang, M.-X.; Xu, Y.-H.; Loh, T.-P. Org. Lett. 2013, 15, 5531.
20. [20]
  Xu, Y.-H.; Lu, J.; Loh, T.-P. J. Am. Chem. Soc. 2009, 131, 1372.Xu, Y.-H.; Lu, J.; Loh, T.-P. J. Am. Chem. Soc. 2009, 131, 1372.
21. [21]
  Xu, Y.-H.; Wang, W.-J.; Wen, Z.-K.; Hartley, J. J.; Loh, T.-P. Tetrahedron Lett. 2010, 51, 3504.Xu, Y.-H.; Wang, W.-J.; Wen, Z.-K.; Hartley, J. J.; Loh, T.-P. Tetrahedron Lett. 2010, 51, 3504.
22. [22]
  Zhang, Y.; Cui, Z.; Li, Z.; Liu, Z.-Q. Org. Lett. 2012, 14, 1838.Zhang, Y.; Cui, Z.; Li, Z.; Liu, Z.-Q. Org. Lett. 2012, 14, 1838.
23. [23]
  Boultadakis-Arapinis, M.; Hopkinson, M. N.; Glorius, F. Org. Lett. 2014, 16, 1630.Boultadakis-Arapinis, M.; Hopkinson, M. N.; Glorius, F. Org. Lett. 2014, 16, 1630.
24. [24]
  Liang, Q.-J.; Yang, C.; Meng, F.-F.; Jiang, B.; Xu, Y.-H.; Loh, T.-P. Angew. Chem. Int. Ed. 2017, 56, 5091.Liang, Q.-J.; Yang, C.; Meng, F.-F.; Jiang, B.; Xu, Y.-H.; Loh, T.-P. Angew. Chem. Int. Ed. 2017, 56, 5091.
25. [25]
  Misha, N. K.; Sharma, S.; Park, J.; Han, S.; Kim, I. S. ACS Catal. 2017, 7, 2821.Misha, N. K.; Sharma, S.; Park, J.; Han, S.; Kim, I. S. ACS Catal. 2017, 7, 2821.
26. [26]
  Gensch, T.; Vásquez-Céspedes, S.; Yu, D.-G.; Glorius, F. Org. Lett. 2015, 17, 3714.Gensch, T.; Vásquez-Céspedes, S.; Yu, D.-G.; Glorius, F. Org. Lett. 2015, 17, 3714.
27. [27]
  Kim, M.; Han, S. H.; Kim, I. S. Chem. Commun. 2014, 50, 11303.Kim, M.; Han, S. H.; Kim, I. S. Chem. Commun. 2014, 50, 11303.
28. [28]
  Wu, X.; Ji, H. Org. Chem. 2018, 83, 12094.Wu, X.; Ji, H. Org. Chem. 2018, 83, 12094.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

基于烯烃碳-氢键活化的碳-碳交叉偶联反应

通讯作者: 赵明,Email:zhaomnwu@126.com

English

C—C Cross Coupling Reaction Based on Olefinic C-H Bond Activation

Corresponding author: Ming Zhao, zhaomnwu@126.com

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

基于烯烃碳-氢键活化的碳-碳交叉偶联反应

通讯作者: 赵明,Email:zhaomnwu@126.com

English

C—C Cross Coupling Reaction Based on Olefinic C-H Bond Activation

Corresponding author: Ming Zhao, zhaomnwu@126.com

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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