通过自由基历程烯烃1,2-双官能团化反应同时构建C—O键和C

引用本文: 吴丹清, 刘佳俊, 李天宇, 徐大振, 苗志伟. 通过自由基历程烯烃1,2-双官能团化反应同时构建C—O键和C—X键研究进展[J]. 大学化学, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087 shu

Citation: Danqing Wu, Jiajun Liu, Tianyu Li, Dazhen Xu, Zhiwei Miao. Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways[J]. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087 shu

通过自由基历程烯烃1,2-双官能团化反应同时构建C—O键和C—X键研究进展

南开大学化学学院, 元素有机化学国家重点实验室, 天津 300071
基金项目:
国家自然科学基金面上项目(22071113)；福建省南平市科技项目(N2020Z008)

摘要: 通过自由基途径的烯烃1,2-双官能团化反应是有机合成中从烯烃直接构建C—X (X = C, N, O…)键的重要手段，其优点包括良好的区域选择性、步骤经济性和原子经济性，符合绿色化学的发展要求。含有碳-氧键的有机功能化合物种类很多，发展简单高效构建碳-氧键的合成方法是有机化学家广泛关注的研究领域。本文综述了在构建碳-氧键的同时，构建碳-碳键、碳-氮键、碳-硫键和碳-卤键的反应研究进程，并对该领域的未来发展方向进行了展望。

关键词:

English

Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
Received Date: 23 March 2024
Revised Date: 21 May 2024
Available Online: 29 May 2024

Abstract: The 1,2-difunctionalization of olefins via radical pathways is a crucial method in organic synthesis for the direct formation of C—X (X = C, N, O, etc.) bonds from olefins. This approach offers several advantages, including high regioselectivity, step economy, and atom economy, making it compatible with the principles of green chemistry. The development of simple and efficient methods for constructing carbon-oxygen bonds is a significant area of interest in organic chemistry due to the prevalence of organic functional compounds containing these bonds. This review summarizes the recent progress in constructing carbon-oxygen bonds concurrently with carbon-carbon, carbon-nitrogen, carbon-sulfur, and carbon-halogen bonds. Additionally, the article discusses the future directions for research in this field.

Key words:

1. [1]
  Huang, H. M.; Xie, Y. J.; Hu, J. H.; Xie, P.; Qian, B. J. Am. Chem. Soc. 2013, 135, 18327.Huang, H. M.; Xie, Y. J.; Hu, J. H.; Xie, P.; Qian, B. J. Am. Chem. Soc. 2013, 135, 18327.
2. [2]
  Dagousset, G.; Barthelemy, A. L.; Tuccio, B.; Magnier, E. Angew. Chem. Int. Ed. 2018, 57, 13790.Dagousset, G.; Barthelemy, A. L.; Tuccio, B.; Magnier, E. Angew. Chem. Int. Ed. 2018, 57, 13790.
3. [3]
  Shi, X. D.; Zhang, S. Y.; Wang, C. H.; Ye, X. H. Angew. Chem. Int. Ed. 2020, 59, 20470.Shi, X. D.; Zhang, S. Y.; Wang, C. H.; Ye, X. H. Angew. Chem. Int. Ed. 2020, 59, 20470.
4. [4]
  Shenvi, R. A.; Crossley, S. W. M.; Obradors, C.; Martinez, R. M. Chem. Rev. 2016, 116, 8912.Shenvi, R. A.; Crossley, S. W. M.; Obradors, C.; Martinez, R. M. Chem. Rev. 2016, 116, 8912.
5. [5]
  Zhu, S. Q.; Tu, H. Y.; Qing, F. L.; Chu, L. L. Synthesis 2020, 52, 1346.Zhu, S. Q.; Tu, H. Y.; Qing, F. L.; Chu, L. L. Synthesis 2020, 52, 1346.
6. [6]
  Hemric, B. N. Org. Biomol. Chem. 2021, 19, 46.Hemric, B. N. Org. Biomol. Chem. 2021, 19, 46.
7. [7]
  Vessally, E.; Ebadi, A.; Hossaini, Z.; Heravi, M. R. P.; Azizi, B. RSC Adv. 2021, 11, 13138.Vessally, E.; Ebadi, A.; Hossaini, Z.; Heravi, M. R. P.; Azizi, B. RSC Adv. 2021, 11, 13138.
8. [8]
  Sodeoka, M.; Egami, H. Angew. Chem. Int. Ed. 2014, 53, 8294.Sodeoka, M.; Egami, H. Angew. Chem. Int. Ed. 2014, 53, 8294.
9. [9]
  Sigman, M. S.; Jensen, K. H. Org. Biomol. Chem. 2008, 6, 4083.Sigman, M. S.; Jensen, K. H. Org. Biomol. Chem. 2008, 6, 4083.
10. [10]
  Chen, Q. Y.; Guo, Y.; Zhao, Z. G.; Li, L.; Huang, M. W.; Liu, C.; Xiao, J. C. Org. Lett. 2015, 17, 4714.Chen, Q. Y.; Guo, Y.; Zhao, Z. G.; Li, L.; Huang, M. W.; Liu, C.; Xiao, J. C. Org. Lett. 2015, 17, 4714.
11. [11]
  Muñiz, K. Chem. Soc. Rev. 2004, 33, 166.Muñiz, K. Chem. Soc. Rev. 2004, 33, 166.
12. [12]
  Sigman, M. S.; Jensen, K. H. Org. Biomol. Chem. 2008, 6, 4083.Sigman, M. S.; Jensen, K. H. Org. Biomol. Chem. 2008, 6, 4083.
13. [13]
  Lei, A. W.; Huang, Z. L.; Jin, L. Q.; Feng, Y.; Peng, Pan.; Yi. H. Angew. Chem. Int. Ed. 2013, 52, 7151.Lei, A. W.; Huang, Z. L.; Jin, L. Q.; Feng, Y.; Peng, Pan.; Yi. H. Angew. Chem. Int. Ed. 2013, 52, 7151.
14. [14]
  Li, J. H.; Song, L. J.; Jiang, S. S.; Gu, C. C.; Li, Y.; Dong, Y. X. Org. Lett. 2018, 20, 7594.Li, J. H.; Song, L. J.; Jiang, S. S.; Gu, C. C.; Li, Y.; Dong, Y. X. Org. Lett. 2018, 20, 7594.
15. [15]
  Mandal, S. K.; Swain, A. K.; Ahmed, J.; Govindarajan, R. J. Org. Chem. 2019, 84, 13490.Mandal, S. K.; Swain, A. K.; Ahmed, J.; Govindarajan, R. J. Org. Chem. 2019, 84, 13490.
16. [16]
  Li, S. H.; Li, Q. K.; Huang, R.; Meng, B. Y.; Peng, D. Q.; Wang, S. H.; Liu, S. H.; Fan, W. ACS. Catal. 2020, 10, 4012.Li, S. H.; Li, Q. K.; Huang, R.; Meng, B. Y.; Peng, D. Q.; Wang, S. H.; Liu, S. H.; Fan, W. ACS. Catal. 2020, 10, 4012.
17. [17]
  Jin, C.; Yu, C. M.; Yan, Z. Y.; Huang, P. Y.; Shi, X. Y.; Zhuang, X. H.; Zhu, R.; Sun, B. Org. Lett. 2021, 23, 617.Jin, C.; Yu, C. M.; Yan, Z. Y.; Huang, P. Y.; Shi, X. Y.; Zhuang, X. H.; Zhu, R.; Sun, B. Org. Lett. 2021, 23, 617.
18. [18]
  Chemler, S. R.; Kim, J. W.; Fuller, P. H. J. Am. Chem. Soc. 2008, 130, 17638.Chemler, S. R.; Kim, J. W.; Fuller, P. H. J. Am. Chem. Soc. 2008, 130, 17638.
19. [19]
  Zhang, W. B.; Yang, G. Q.; Zhang, X. H.; Wu, L.; Li, Y.; Kou, X. Z. Org. Lett. 2015, 17, 5566.Zhang, W. B.; Yang, G. Q.; Zhang, X. H.; Wu, L.; Li, Y.; Kou, X. Z. Org. Lett. 2015, 17, 5566.
20. [20]
  Wang, Q.; Chen, A. W.; Hemric, B. N. ACS Catal. 2019, 9, 10070.Wang, Q.; Chen, A. W.; Hemric, B. N. ACS Catal. 2019, 9, 10070.
21. [21]
  Huang, J. M.; Wan, J. L. Org. Lett. 2022, 24, 8914.Huang, J. M.; Wan, J. L. Org. Lett. 2022, 24, 8914.
22. [22]
  Han, J. L.; Wang, Y.; Deng, L. L.; Mei, H. B.; Du, B. N.; Pan, Y. Green Chem. 2018, 20, 3444.Han, J. L.; Wang, Y.; Deng, L. L.; Mei, H. B.; Du, B. N.; Pan, Y. Green Chem. 2018, 20, 3444.
23. [23]
  Sun, J. W.; Ma, D. K.; Yan, J. Y.; Zhang, Z. F. Chin. Chem. Lett. 2019, 30, 1509.Sun, J. W.; Ma, D. K.; Yan, J. Y.; Zhang, Z. F. Chin. Chem. Lett. 2019, 30, 1509.
24. [24]
  Gao, B.; Liu, X. J.; Yan, Q.; Yang, R. T.; Jiang, T.; Zhang, X. L. Synthesis 2022, 54, 2258.Gao, B.; Liu, X. J.; Yan, Q.; Yang, R. T.; Jiang, T.; Zhang, X. L. Synthesis 2022, 54, 2258.
25. [25]
  Liu, C. J.; Xia, Y.; Jin, W. W.; Zhang, Y. H.; Wang, B.; Liu, T. X.; Xue, F.; Chen, Z. R. Green Chem. 2022, 24, 3250.Liu, C. J.; Xia, Y.; Jin, W. W.; Zhang, Y. H.; Wang, B.; Liu, T. X.; Xue, F.; Chen, Z. R. Green Chem. 2022, 24, 3250.
26. [26]
  Majee, A.; Zyryanov, G. V.; Hajra, A.; Kundu, S. K.; Santra, S.; Chakraborty, N. RSC Adv. 2015, 5, 56780.Majee, A.; Zyryanov, G. V.; Hajra, A.; Kundu, S. K.; Santra, S.; Chakraborty, N. RSC Adv. 2015, 5, 56780.
27. [27]
  Li, J. H.; Song, R. J.; Wan, C. Org. Lett. 2019, 21, 2800.Li, J. H.; Song, R. J.; Wan, C. Org. Lett. 2019, 21, 2800.
28. [28]
  Li, J. H.; Song, R. J.; Zhang, T. T.; Luo, M. J.; Li, Y. Org. Lett. 2020, 22, 7250.Li, J. H.; Song, R. J.; Zhang, T. T.; Luo, M. J.; Li, Y. Org. Lett. 2020, 22, 7250.
29. [29]
  Li, H. L.; Li, Z.Q.; Zhai, L. L.; Fang, B. W. Tetrahedron Letters. 2023, 126, 154647.Li, H. L.; Li, Z.Q.; Zhai, L. L.; Fang, B. W. Tetrahedron Letters. 2023, 126, 154647.

扫一扫看文章

计量

PDF下载量: 0
文章访问数: 141
HTML全文浏览量: 16

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

通过自由基历程烯烃1,2-双官能团化反应同时构建C—O键和C—X键研究进展

English

Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways

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？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

通过自由基历程烯烃1,2-双官能团化反应同时构建C—O键和C—X键研究进展

English

Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways

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？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs