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Aggregation Enabled Alkene Insertion into Carbon--Halogen Bonds
  • +9
  • Meng-Yao Li,
  • Xiao-Mei Nong,
  • Han Xiao,
  • Ao Gu,
  • Shuyang Zhai,
  • Jiatong Li,
  • Ge Zhang,
  • Ze-Jian Xue,
  • Yingbin Liu,
  • Chunsen Li,
  • Guo-Qiang Lin,
  • Chen-Guo Feng
Meng-Yao Li
Shanghai Jiao Tong University School of Medicine Affiliated Renji Hospital

Corresponding Author:limy@sioc.ac.cn

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Xiao-Mei Nong
Shanghai Jiao Tong University School of Medicine Affiliated Renji Hospital
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Han Xiao
Chinese Academy of Sciences Fujian Institute of Research on the Structure of Matter
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Ao Gu
Shanghai Jiao Tong University School of Medicine Affiliated Renji Hospital
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Shuyang Zhai
Shanghai Jiao Tong University School of Medicine Affiliated Renji Hospital
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Jiatong Li
Shanghai Jiao Tong University School of Medicine Affiliated Renji Hospital
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Ge Zhang
Shanghai Institute of Organic Chemistry Chinese Academy of Sciences
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Ze-Jian Xue
Shanghai Institute of Organic Chemistry Chinese Academy of Sciences
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Yingbin Liu
Shanghai Jiao Tong University School of Medicine Affiliated Renji Hospital
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Chunsen Li
Chinese Academy of Sciences Fujian Institute of Research on the Structure of Matter
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Guo-Qiang Lin
Shanghai University of Traditional Chinese Medicine
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Chen-Guo Feng
Shanghai University of Traditional Chinese Medicine
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Abstract

Molecular aggregation affects the electronic interactions between molecules and has emerged as a powerful tool in material science. Molecular aggregation finds wide applications in the research of new physical effects; however, its value for chemical reaction development has been far less explored. Herein, we report the development of aggregation-enabled alkene insertion into carbon–halogen bonds. The spontaneous cleavage of C–X (X = Cl, Br, or I) bonds generates an intimate ion pair, which can be quickly captured by alkenes in the aggregated state. Additional catalysts or promoters are not necessary under such circumstances, and solvent quenching experiments indicate that the aggregated state is critical for initiating such sequences. The ionic insertion mode and the intimate ion pair mechanism are supported by mechanistic studies, density functional theory calculations, and symmetry-adapted perturbation theory analysis. Results show that the non-aggregated state may quench the transition state and terminate the insertion process.
07 Mar 2023Submitted to Aggregate
07 Mar 2023Submission Checks Completed
07 Mar 2023Assigned to Editor
08 Mar 2023Reviewer(s) Assigned
18 Mar 2023Review(s) Completed, Editorial Evaluation Pending
22 Mar 2023Editorial Decision: Revise Major
26 Mar 20231st Revision Received
26 Mar 2023Submission Checks Completed
26 Mar 2023Assigned to Editor
27 Mar 2023Reviewer(s) Assigned
09 Apr 2023Review(s) Completed, Editorial Evaluation Pending
10 Apr 2023Editorial Decision: Accept