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Theoretical investigation on the rhodium-catalyzed coupling reaction of ketoxime with 1,3-enynes: [4 + 1] vs. [4 + 2] annulation
  • Xiao Yun,
  • Zhangyu Yu,
  • Tao Liu
Xiao Yun
Qufu Normal University
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Zhangyu Yu
Jining University
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Tao Liu
Jining University
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Abstract

The mechanisms of rhodium-catalyzed coupling reaction of ketoxime and 1,3-enynes were investigated by employing the density functional theory (DFT) calculations. Different 1,3-enynes would lead to different annulation products. Reaction A undergoes five sequential steps (C-H activation, 1,3-enyne migratory insertion, 1,4-Rh migration, cyclization, and deprotonation) to lead to [4 + 1] annulation product. Whereas, due to the electronic effect, the process generating [4 + 2] product in reaction A is restricted. In contrast, the electron-withdrawing group of N(Me)2 group in 1,3-enyne would bring about the [4 + 2] annulation product in reaction B. Our calculated results indicate that no [4 + 1] annulation product could be obtained in reaction C, in agreement with the experimental observation that the cis-allyl hydrogen in 1,3-enyne is crucial for the [4 + 1] annulation reaction.

Peer review status:Published

18 Jun 2020Submitted to International Journal of Quantum Chemistry
19 Jun 2020Submission Checks Completed
19 Jun 2020Assigned to Editor
10 Jul 2020Reviewer(s) Assigned
21 Jul 2020Review(s) Completed, Editorial Evaluation Pending
22 Jul 2020Editorial Decision: Revise Minor
03 Aug 20201st Revision Received
03 Aug 2020Submission Checks Completed
03 Aug 2020Assigned to Editor
03 Aug 2020Reviewer(s) Assigned
03 Aug 2020Review(s) Completed, Editorial Evaluation Pending
03 Aug 2020Editorial Decision: Accept
29 Aug 2020Published in International Journal of Quantum Chemistry. 10.1002/qua.26449