Citation: Lingling Liu, Hongli Wu, Genping Huang. Mechanism and selectivity of nickel-catalyzed [3 + 2] cycloaddition of cyclopropenones and α, β-unsaturated ketones: A computational study[J]. Chinese Chemical Letters, ;2021, 32(10): 3015-3018. doi: 10.1016/j.cclet.2021.04.006 shu

Mechanism and selectivity of nickel-catalyzed [3 + 2] cycloaddition of cyclopropenones and α, β-unsaturated ketones: A computational study

Department of Chemistry, School of Science and Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, Tianjin 300072, China

gphuang@tju.edu.cn

Received Date: 25 February 2021
Revised Date: 31 March 2021
Accepted Date: 1 April 2021
Available Online: 3 April 2021

Figures(5)

Density functional theory calculations have been performed to investigate the nickel-catalyzed [3 + 2] cycloaddition of cyclopropenones and α, β-unsaturated ketones. The computations show that the overall catalytic cycle consists of four major steps, including: (1) C-C oxidative addition of the cyclopropenone to afford the four-membered nickelacycle, (2) isomerization, (3) migratory insertion via a 4, 1-insertion fashion, and (4) C-C reductive elimination to deliver the [3 + 2] cycloaddition product. The enantioselectivity is mainly attributed to the π-π interaction between the diphenylcyclopropenone moiety and the phenyl substituent of the oxazoline ring of the ligand. The chemoselectivity of the C = O versus C = C insertion was rationalized in terms of the steric effect.
- Nickel catalyst,
- Cycloaddition,
- Mechanism,
- Selectivity,
- DFT calculations
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