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Original Research ARTICLE Provisionally accepted The full-text will be published soon. Notify me

Front. Chem. | doi: 10.3389/fchem.2019.00596

Mechanistic Features in Al(I)−mediated Oxidative Addition of aryl C−F Bonds: Insights From DFT Calculations

xiangfei zhang1, ping li1,  Binju Wang1* and  Zexing Cao1*
  • 1Xiamen University, China

The oxidative addition of a range of robust aryl C−F bonds to a single Al(I) center supported by a (NacNac)− bidentate ligand ((NacNac)− = [ArNC(Me)CHC(Me)NAr]− and Ar = 2,6−Pri2C6H3) have been explored by density functional theory calculations. Our calculations demonstrate that the Al(I) center-mediated C−F insertion generally proceeds via the concerted mechanism that involve both the donation ( ) and back−donation ( ) interactions. In addition, the predicted free energy barriers for the C−F bond activation show good agreement with the experimental information available. Finally, the comparative studies show that B(I) is the most active among group III metals (B, Al, Ga), thus supplying a testable prediction for experiments.

Keywords: C−F Bonds, Oxidative Addition, DFT calculations, Al(I), Mechanism

Received: 26 Jun 2019; Accepted: 12 Aug 2019.

Copyright: © 2019 zhang, li, Wang and Cao. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence:
Prof. Binju Wang, Xiamen University, Xiamen, 361005, Fujian Province, China, wangbinju2018@xmu.edu.cn
Prof. Zexing Cao, Xiamen University, Xiamen, 361005, Fujian Province, China, zxcao@xmu.edu.cn