Chemical Papers

, Volume 73, Issue 4, pp 995–1001 | Cite as

Activation and recyclization of a benzocyclobutenone derivative catalyzed by a chiral Rh(I) complex based on DFT investigations

  • Xueli ChengEmail author
  • Feng Li
  • Yanyun Zhao
  • Zhiguo Wang
  • Chang-An Wang
Original Paper


The R- and S-activation and cyclization channels of an achiral benzocyclobutenone derivative to a pair of enantiomers with poly-fused rings were investigated systematically based on full optimization with the BP86 functional in gas phase and the M06 functional in tetrahydrofuran (THF). Both the BP86 and M06 methods show that the R-channel is energetically more favorable than the S-channel in gas phase and in THF. The rate-determining step for the R-channel is the C–C activation with a barrier of 17.2 kcal/mol in THF and 11.8 kcal/mol in gas phase, but for the S-channel, the rate-determining step is the pentatomic ring formation process with a barrier of 25.6 kcal/mol in THF and 22.3 kcal/mol in gas phase.


C–C activation Olefin carboacylation BP86 M06 



This work was supported by the National Natural Science Foundation of China (21502136), the Natural Science Foundation of Shandong Province (ZR2017LB010) and the Scientific Research Initial Foundation for Introduction of Talent of Taishan University (Y-01-2013010).

Supplementary material

11696_2018_641_MOESM1_ESM.doc (624 kb)
Supplementary material 1 (DOC 624 kb)


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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringTaishan UniversityTai’anChina
  2. 2.Department of Academic ResearchTaishan UniversityTai’anChina
  3. 3.Institute of Aging Research, School of MedicineHangzhou Normal UniversityHangzhouChina

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