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| DFT Investigation on the Enantioselectivity of Olefin Carboacylation Catalyzed by a Rh(I) Complex |
| CHENG Xue-Li;LI Li-Qing;HAN Yin-Feng;TAN Qing-Long;XIA Qi-Ying |
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) |
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Abstract 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.
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Received: 23 May 2019
Published: 13 April 2020
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Fund:This work was jointly supported by the National Natural Science Foundation of China (No. 21571137), the Natural Science Foundation of Shandong Province (ZR2017LB010) and the Science and Technology Planning Project (Guidance Plan) of Tai’an City (Nos. 2018GX0041 and 2018GX0073)
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Corresponding Authors:
x_cheng@tsu.edu.cn
E-mail: x_cheng@tsu.edu.cn
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2020, Vol. 39 
