Citation: Yue Zhao, Yanfei Li, Tao Xiong. Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones[J]. University Chemistry, ;2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001 shu

Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones

Department of Chemistry, Northeast Normal University, Changchun 130024, China

Corresponding author: Tao Xiong, xiongt626@nenu.edu.cn
Received Date: 1 September 2023
Revised Date: 16 January 2024

The addition reactions of organometallics such as organolithium reagents, Grignard reagent, organocopper reagents and organoaluminum reagents to aldehydes and ketones are crucial in organic chemistry, and represent one of most classic methods for C―C bond construction. However, such organometallics are limited in their wide applications due to their poor functional group compatibility, sensitivity to water and air and difficulties in storage. As a consequence, the development of new methods with stable, readily available unsaturated hydrocarbons instead of organometallics to participate in various transformations have attracted significant attention. In this article, we primarily focus on the methodology of using unsaturated hydrocarbons converting into catalytic loading of organocopper intermediates under copper-hydride catalysis, instead of traditional stoichiometric amount of organometallics, to implement the addition reactions to aldehydes and ketones. This approach effectively overcomes the limitations associated with traditional methodologies. The introduction of these reactions can enrich and expand the content of nucleophilic addition knowledge in basic teaching processes, broaden students’ perspectives and thinking, facilitate their understanding of the current developments in the field, and stimulate their interest.
- Copper hydride catalysis,
- Unsaturated hydrocarbons,
- Organometallics,
- Nucleophilic addition
1. [1]
2. [2]
  Liu, R. R.; Buchwald, S. L. Acc. Chem. Res.2020, 53, 1229.
3. [3]
  Xiong, T.; Li, Y. Copper(I) Hydride Catalyzed Transformations. In Science of Synthesis Base-Metal Catalysis 1; Thieme: Stuttgart, Germany, 2022.
4. [4]
  Jang, W. J.; Yun, J. Angew. Chem. Int. Ed.2018, 57, 12116.
5. [5]
  Li, J.; Shao, X.; Tseng, L.; Malcolmson, S. J. J. Am. Chem. Soc.2018, 140, 598.
6. [6]
  Dong, Y.; Schuppe, A. W.; Mai, B. K.; Liu, P.; Buchwald, S. L. J. Am. Chem. Soc. 2022, 144, 5985.
7. [7]
  Li, C.; Liu, R.; Jesikiewicz, L. T.; Yang, Y.; Liu, P.; Buchwald, S. L. J. Am. Chem. Soc. 2019, 141, 5062.
8. [8]
  Fu, B.; Yuan, X.; Li, Y.; Zhang, Q.; Xiong, T.; Zhang, Q. Org. Lett. 2019, 21, 3576.
9. [9]
  Yang, Y.; Perry, I. B.; Lu, G.; Liu, P.; Buchwald, S. L. Science 2016, 353, 144.
10. [10]
  Liu, R. Y.; Zhou, Y.; Yang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2019, 141, 2251.
11. [11]
  Collins, S.; Sieber, J. Org. Lett.2023, 25, 1425.
12. [12]
  Zhong, F.; Pan, Z.-Z.; Zhou, S.-W.; Zhang, H.-J.; Yin, L. J. Am. Chem. Soc. 2021, 143, 4556.
13. [13]
  Gargaro, S.; Klake, R. K.; Sieber, J. D. Org. Lett. 2023, 25, 4644.
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