Citation: Pengzi Wang, Wenjing Xiao, Jiarong Chen. Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction[J]. University Chemistry, ;2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090 shu

Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction

College of Chemistry, Central China Normal University, Wuhan 430079, China

Received Date: 24 June 2024
Revised Date: 22 July 2024

Transition metal-catalyzed carbon-heteroatom bond formation is a crucial area in synthetic organic chemistry. The Kharasch-Sosnovsky reaction, catalyzed by copper, facilitates the conversion of olefins to allylic esters using tert-butyl peroxybenzoate as both an oxidant and oxygen source. In line with the “National Dual-Carbon Strategy”, the development of green and efficient catalytic systems for carbon-based transformations has become a key focus in organic chemistry. In this context, the Kharasch-Sosnovsky-type reaction has witnesses notable advances regarding asymmetric versions, ligand design, substrate scope expansion, and sustainable conditions. By surveying the cutting-edge chemical research, this paper presents a concise overview of the discovery and new progress of Kharasch-Sosnovsky reaction. It is hoped that this review can not only enhance students’ comprehension of fundamental organic chemistry concepts, but also effectively fill the gaps in existing textbooks, achieving a deep integration of basic chemical knowledge with cutting-edge research in the discipline.
- Kharasch-Sosnovsky reaction,
- Copper catalysis,
- Olefin oxidation,
- Asymmetric radical reaction
1. [1]
  Kharasch, M. S.; Sosnovsky, G. J. Am. Chem. Soc. 1958, 80, 756.
2. [2]
  Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1959, 81, 5819.
3. [3]
4. [4]
  Kochi, J. K. J. Am. Chem. Soc. 1962, 84, 774.
5. [5]
  Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831.
6. [6]
  Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945.
7. [7]
  Eames, J.; Watkinson, M. Angew. Chem. Int. Ed. 2001, 40, 3567.
8. [8]
  Zhu, N.; Yao, H.; Zhang, X.; Bao, H. Chem. Soc. Rev. 2024, 53, 2326.
9. [9]
  Fan, L.-F.; Liu, R.; Ruan, X.-Y.; Wang, P.-S.; Gong, L.-Z. Nat. Synth. 2022, 1, 946.
10. [10]
  Zhu, X.; Jian, W.; Huang, M.; Li, D.; Li, Y.; Zhang, X.; Bao, H. Nat. Commun. 2021, 12, 6670.
11. [11]
  Ciamician, G. Science 1912, 36, 385.
12. [12]
13. [13]
  Chen, J.; Liang, Y.-J.; Wang, P.-Z.; Li, G.-Q.; Zhang, B.; Qian, H.; Huan, X.-D.; Guan, W.; Xiao, W.-J.; Chen, J.-R. J. Am. Chem. Soc. 2021, 143, 13382.
14. [14]
  Wang, P.-Z.; Wu, X.; Cheng, Y.; Jiang, M.; Xiao, W.-J.; Chen, J.-R. Angew. Chem. Int. Ed. 2021, 60, 22956.
1. [1]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
2. [2]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
3. [3]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
4. [4]
  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. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
5. [5]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
6. [6]
  .
  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): -.
7. [7]
  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
8. [8]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
9. [9]
  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
10. [10]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
11. [11]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
12. [12]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
13. [13]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
14. [14]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
15. [15]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
16. [16]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
17. [17]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
18. [18]
  Tong Zhou , Jun Li , Zitian Wen , Yitian Chen , Hailing Li , Zhonghong Gao , Wenyun Wang , Fang Liu , Qing Feng , Zhen Li , Jinyi Yang , Min Liu , Wei Qi . Experiment Improvement of “Redox Reaction and Electrode Potential” Based on the New Medical Concept. University Chemistry, 2024, 39(8): 276-281. doi: 10.3866/PKU.DXHX202401005
19. [19]
  Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, 2024, 39(8): 351-358. doi: 10.3866/PKU.DXHX202401031
20. [20]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(56)
HTML views(14)

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