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Transition Metal Chemistry

, Volume 44, Issue 6, pp 545–553 | Cite as

A theoretical study of Fe(PMe3)4-catalyzed anti-Markovnikov addition of aromatics to alkenes to provide linear alkylation products

  • Hongping Zhang
  • Xueyan Zhu
  • Mian WangEmail author
  • Bu-Ming Liu
  • Yan Huang
  • Jianyi WangEmail author
Article
  • 54 Downloads

Abstract

The mechanisms and regioselectivities of Fe(0)-catalyzed alkylation of aromatic compounds with alkenes were explored by DFT calculations. Our calculations show that these systems tend to undergo anti-Markovnikov addition. The influence of steric effects on the reaction mechanism has been investigated. The results indicate that the reaction is more likely to provide the linear product with dissociation of the 1PMe3 ligand. The reductive elimination is the rate-determining step of the whole process, such that the electrostatic interactions of the reaction site and the steric hindrance of the trimethylsilyl groups are favorable for the anti-Markovnikov rather than the Markovnikov addition pathway. Our calculations provide insights into the regioselective origin of the alkylation of aromatic compounds mediated by Fe(PMe3)4.

Notes

Acknowledgements

This work was financially supported by Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards (201602), the Scientific Research Fund of Guangxi Education Department (2018KY0044) and the Scientific Research Fund of Guangxi University (XJZ170410). The computational resources are partly provided by Multifunction Computer Center of Guangxi University.

Supplementary material

11243_2019_338_MOESM1_ESM.docx (1.1 mb)
Supplementary material 1 (DOCX 1135 kb)

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Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Medical CollegeGuangxi UniversityNanningChina
  2. 2.Guangxi Institute for Food and Drug ControlNanningChina
  3. 3.School of Chemistry and Chemical EngineeringGuangxi UniversityNanningChina
  4. 4.Guangxi Key Laboratory of Traditional Chinese Medicine Quality StandardsNanningChina

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