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Metal-free alkyne annulation enabling π-extension of boron-doped polycyclic aromatic hydrocarbons.
Anitha, Mandala; Chin, To-Jen; Liu, Guan-Cheng; Hsieh, Chi-Tien; Wang, Kuan-Hua; Li, Shu-Li; Cheng, Mu-Jeng; Farrell, Jeffrey M.
Afiliación
  • Anitha M; Department of Chemistry, National Taiwan University No. 1, Sec. 4, Roosevelt Rd. Taipei 10617 Taiwan farrell@ntu.edu.tw.
  • Chin TJ; Department of Chemistry, National Taiwan University No. 1, Sec. 4, Roosevelt Rd. Taipei 10617 Taiwan farrell@ntu.edu.tw.
  • Liu GC; Department of Chemistry, National Taiwan University No. 1, Sec. 4, Roosevelt Rd. Taipei 10617 Taiwan farrell@ntu.edu.tw.
  • Hsieh CT; Department of Chemistry, National Cheng Kung University Tainan 701 Taiwan.
  • Wang KH; Department of Chemistry, National Cheng Kung University Tainan 701 Taiwan.
  • Li SL; Department of Chemistry, National Taiwan University No. 1, Sec. 4, Roosevelt Rd. Taipei 10617 Taiwan farrell@ntu.edu.tw.
  • Cheng MJ; Department of Chemistry, National Cheng Kung University Tainan 701 Taiwan.
  • Farrell JM; Department of Chemistry, National Taiwan University No. 1, Sec. 4, Roosevelt Rd. Taipei 10617 Taiwan farrell@ntu.edu.tw.
Chem Sci ; 2024 Sep 16.
Article en En | MEDLINE | ID: mdl-39296993
ABSTRACT
A C-H functionalizing annulation reaction of boron-doped polycyclic aromatic hydrocarbons (PAHs) with alkynes is described. This metal-free π-extension provides a new synthetic route to fusion atom B-doped polycyclic aromatic hydrocarbons (PAHs) that is demonstrated with the synthesis of a family of new, functionalized, structurally constrained 6a,15a-diborabenzo[tuv]naphtho[2,1-b]picenes. These annulation products exhibit deep LUMO energy levels, strong visible-range absorptions, and sterically accessible π-systems that can adopt herringbone or π-stacked solid-state structures based on choice of substituents. From regioselectivity and DFT calculations, we propose an annulation mechanism involving intramolecular electrophilic aromatic substitution of a zwitterionic intermediate.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido