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

Xiao-Na Ke ,  Casi M. Schienebeck ,  Chen-Chen Zhou ,  Xiu-Fang Xu ,  Wei-Ping Tang

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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

    • 通讯作者: Xiu-Fang Xu,
    Wei-Ping Tang,
  • 基金项目:

    We are grateful to Tianjin Natural Science Foundation (No. 14JCYBJC20100 X.X.) (No. 14JCYBJC20100 X.X.)

    NIH (No. R01GM088285 W.T.) for financial support. (No. R01GM088285 W.T.)

摘要: 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.

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    21. [21] Computational studies involving the active catalyst Rh(CO)Cl which derives from dissociation of the dimer [RhCl(CO)2]2: (a) ZX. Yu, P.A. Wender, K.N. Houk, On the mechanism of [Rh(CO)2Cl]2-catalyzed intermolecular (5 + 2) reactions between vinylcyclopropanes and alkynes, J. Am. Chem. Soc. 126 (2004) 9154-9155; (b) Z.X. Yu, P.H.Y. Cheong, P. Liu, et al., Origins of differences in reactivities of alkenes, alkynes, and allenes in [Rh(CO)2Cl]2-catalyzed (5 + 2) cycloaddition reactions with vinylcyclopropanes, J. Am. Chem. Soc. 130 (2008) 2378-2379; (c) P. Liu, P.H.Y. Cheong, Z.X. Yu, P.A. Wender, K.N. Houk, Substituent effects, reactant preorganization, and ligand exchange control the reactivity in Rh(I)-catalyzed (5 + 2) cycloadditions between vinylcyclopropanes and alkynes, Angew. Chem. Int. Ed. 47 (2008) 3939-3941; (d) X. Xu, P. Liu, A. Lesser, et al., Ligand effects on rates and regioselectivities of Rh(I)-catalyzed (5 + 2) cycloadditions: a computational study of cyclooctadiene and dinaphthocyclooctatetraene as ligands, J. Am. Chem. Soc. 134 (2012) 11012-11025.[21] Computational studies involving the active catalyst Rh(CO)Cl which derives from dissociation of the dimer [RhCl(CO)2]2: (a) ZX. Yu, P.A. Wender, K.N. Houk, On the mechanism of [Rh(CO)2Cl]2-catalyzed intermolecular (5 + 2) reactions between vinylcyclopropanes and alkynes, J. Am. Chem. Soc. 126 (2004) 9154-9155; (b) Z.X. Yu, P.H.Y. Cheong, P. Liu, et al., Origins of differences in reactivities of alkenes, alkynes, and allenes in [Rh(CO)2Cl]2-catalyzed (5 + 2) cycloaddition reactions with vinylcyclopropanes, J. Am. Chem. Soc. 130 (2008) 2378-2379; (c) P. Liu, P.H.Y. Cheong, Z.X. Yu, P.A. Wender, K.N. Houk, Substituent effects, reactant preorganization, and ligand exchange control the reactivity in Rh(I)-catalyzed (5 + 2) cycloadditions between vinylcyclopropanes and alkynes, Angew. Chem. Int. Ed. 47 (2008) 3939-3941; (d) X. Xu, P. Liu, A. Lesser, et al., Ligand effects on rates and regioselectivities of Rh(I)-catalyzed (5 + 2) cycloadditions: a computational study of cyclooctadiene and dinaphthocyclooctatetraene as ligands, J. Am. Chem. Soc. 134 (2012) 11012-11025.

    22. [22] C.M. Schienebeck, P.J. Robichaux, X. Li, L. Chen, W. Tang, Effect of ester on rhodium-catalyzed intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes, Chem. Commun. 49 (2013) 2616-2618.[22] C.M. Schienebeck, P.J. Robichaux, X. Li, L. Chen, W. Tang, Effect of ester on rhodium-catalyzed intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enynes and alkynes, Chem. Commun. 49 (2013) 2616-2618.

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  • 发布日期:  2015-03-27
  • 收稿日期:  2014-12-15
  • 网络出版日期:  2015-01-22
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