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

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

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.
- Alkenes,
- 1,2-Difunctionalization,
- C—O bond construction,
- Regioselectivity,
- Research progress,
- Radical pathways
1. [1]
  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.
3. [3]
  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.
5. [5]
  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.
7. [7]
  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.
9. [9]
  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.
11. [11]
  Muñiz, K. Chem. Soc. Rev. 2004, 33, 166.
12. [12]
  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.
14. [14]
  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.
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.
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.
18. [18]
  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.
20. [20]
  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.
22. [22]
  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.
24. [24]
  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.
26. [26]
  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.
28. [28]
  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.
1. [1]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
2. [2]
  Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
3. [3]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
4. [4]
  Yuyang Xu , Ruying Yang , Yanzhe Zhang , Yandong Liu , Keyi Li , Zehui Wei . Research Progress of Aflatoxins Removal by Modern Optical Methods. University Chemistry, 2024, 39(11): 174-181. doi: 10.12461/PKU.DXHX202402064
5. [5]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
6. [6]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . 表面硫物种对钯-硫纳米片加氢性能的影响. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-. doi: 10.3866/PKU.WHXB202309043
7. [7]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
8. [8]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
9. [9]
  Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018
10. [10]
  Zongfei YANG , Xiaosen ZHAO , Jing LI , Wenchang ZHUANG . Research advances in heteropolyoxoniobates. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 465-480. doi: 10.11862/CJIC.20230306
11. [11]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
12. [12]
  Yu Guo , Zhiwei Huang , Yuqing Hu , Junzhe Li , Jie Xu . 钠离子电池中铁基异质结构负极材料的最新研究进展. Acta Physico-Chimica Sinica, 2025, 41(3): 2311015-. doi: 10.3866/PKU.WHXB202311015
13. [13]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
14. [14]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
15. [15]
  Yuan GAO , Yiming LIU , Chunhui WANG , Zhe HAN , Chaoyue FAN , Jie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271
16. [16]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
17. [17]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
18. [18]
  Xinxin JING , Weiduo WANG , Hesu MO , Peng TAN , Zhigang CHEN , Zhengying WU , Linbing SUN . Research progress on photothermal materials and their application in solar desalination. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1033-1064. doi: 10.11862/CJIC.20230371
19. [19]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
20. [20]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(596)
HTML views(122)

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