Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction

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Staudt M., Cetin A., Bunch L.

CHEMISTRY-A EUROPEAN JOURNAL, cilt.28, sa.10, 2022 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 28 Sayı: 10
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1002/chem.202102998
  • Dergi Adı: CHEMISTRY-A EUROPEAN JOURNAL
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, MEDLINE, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Anahtar Kelimeler: anilines, drug synthesis, electrocyclic ring-opening, new methodology, transition metal-free, CATALYZED C-N, CONVERSION
  • Van Yüzüncü Yıl Üniversitesi Adresli: Hayır

Özet

Anilines are key constituents in biologically active compounds and often obtained from transition metal-catalyzed coupling of an aryl halide with an amine. In this work, we report a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines starting from 3-tribromomethylcyclopentanone or 3-(2-bromo-2-chloro-1,1,1-trifluoroethyl)cyclopentanone, respectively. The scope of the transformation is shown by application of primary, secondary and aromatic amines. The reaction proceeds in acceptable to high yields (20-81 %), and allows for the synthesis of anilines with substitution patterns otherwise difficult to access.