Citation: Xiao-Na Ke, Casi M. Schienebeck, Chen-Chen Zhou, Xiu-Fang Xu, Wei-Ping Tang. Mechanism and reactivity of rhodium-catalyzed intermolecular [5 + 1] cycloaddition of 3-acyloxy-1,4-enyne (ACE) and CO: A computational study[J]. Chinese Chemical Letters, ;2015, 26(6): 730-734. doi: 10.1016/j.cclet.2015.03.016 shu

Mechanism and reactivity of rhodium-catalyzed intermolecular [5 + 1] cycloaddition of 3-acyloxy-1,4-enyne (ACE) and CO: A computational study

1.
a Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China;
2.
b School of Pharmacy and Department of Chemistry, University of Wisconsin, Madison, WI 53705-2222, USA

Corresponding author: Xiu-Fang Xu, Wei-Ping Tang,
Received Date: 15 December 2014
Available Online: 22 January 2015
Fund Project: We are grateful to Tianjin Natural Science Foundation (No. 14JCYBJC20100 X.X.) (No. 14JCYBJC20100 X.X.)

The first theoretical study on the mechanism of [RhCl(CO)₂]₂-catalyzed [5 + 1] cycloadditions of 3-acyloxy-1,4-enyne (ACE) and CO has been performed using density functional theory (DFT) calculations. The effect of ester on reactivity of this reaction has been investigated. The computational results have revealed that the preferred catalytic cycle involves the sequential steps of 1,2-acyloxy migration, CO insertion, reductive elimination to form ketene intermediate, 6π-electroncyclization, and aromatization to afford the resorcinol product. The 1,2-acyloxy migration is found to be the rate-determining step of the catalytic cycle. The electron-rich p-dimethylaminobenzoate substrate promotes 1,2-acyloxy migration and significantly increases the reactivity by stabilizing the positive charge building up in the oxocyclic transition state.
- [5 + 1] cycloaddition,
- Rhodium catalyst,
- DFT,
- Ester effect
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