Citation: Xue-Li CHENG, Li-Qing LI, Yin-Feng HAN, Qing-Long TAN, Qi-Ying XIA. DFT Investigation on the Enantioselectivity of Olefin Carboacylation Catalyzed by a Rh(Ⅰ) Complex[J]. Chinese Journal of Structural Chemistry, ;2020, 39(4): 630-642. doi: 10.14102/j.cnki.0254-5861.2011-2468 shu

DFT Investigation on the Enantioselectivity of Olefin Carboacylation Catalyzed by a Rh(Ⅰ) Complex

a.
School of Chemistry and Chemical Engineering, Taishan University, Tai'an 271000, China
b.
School of Chemistry, Chemical Engineering and Materials, Zaozhuang University, Zaozhuang 277160, China
c.
School of Chemistry and Chemical Engineering, Linyi University, Linyi 276005, China

Corresponding author: Xue-Li CHENG, x_cheng@tsu.edu.cn Qi-Ying XIA, xiaqiying@163.com
Received Date: 23 May 2019
Accepted Date: 25 February 2020

Fund Project: the National Natural Science Foundation of China 21571137the Natural Science Foundation of Shandong Province ZR2017LB010the Science and Technology Planning Project (Guidance Plan) of Tai'an City 2018GX0041the Science and Technology Planning Project (Guidance Plan) of Tai'an City 2018GX0073

Figures(10)

The C–C bond activation and recyclization of benzocyclobutenone to poly-fused rings catalyzed by the [Rh(R,S-L)]⁺ complex producing the R,S-, S,R-, R,R- and S,S-product were investigated systematically at the BP86/6-31G(d,p) level in gas phase and THF, and the R,S- and S,R-reaction pathways were revisited at the M062X/6-31G(d,p) level in THF. The computational results reveal that THF only marginally alters the free-energy barriers, but elevates the relative energies of all species. The BP86 functional testifies that in both gas phase and THF, the activation of strained C–C bonds bears relatively low free-energy barriers, and the rate-determining steps of S,R- and R,R-channels are different from those of R,S- and S,S-channels. The BP86 functional also predicts that the R,S-channel is energetically most favorable in gas phase, but the S,R-product is dominant in THF. The change of NPA charges can mirror the variation of molecular structures to elucidate reaction mechanisms.
- benzocyclobutenone,
- carboacylation,
- enantioselectivity,
- BP86,
- M06-2X
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沈阳化工大学材料科学与工程学院沈阳 110142