Dehydrogenative Photocyclization of 3-Styryl Indoles to Fused Indole Systems


TAŞKESENLİGİL Y., SARAÇOĞLU N.

Journal of Organic Chemistry, 2024 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1021/acs.joc.4c02103
  • Dergi Adı: Journal of Organic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, Compendex, MEDLINE
  • Atatürk Üniversitesi Adresli: Evet

Özet

The synthesis of 5-aryl- or 5,6-diaryl-11H-benzo[a]carbazoles has been achieved from 3-styryl indoles through catalyst-free photoinitiated dehydrogenative cyclization transformation, providing a range of structurally diverse products in excellent yields under mild conditions. The protocol is also applicable to furan and thiophene samples. This Mallory-type reaction takes place in an argon atmosphere without external oxidants. Finally, detailed mechanistic studies were performed, and kinetic isotope effect experiments indicate that dehydrogenative annulation reaction involves photoinduced 6π-electrocyclic ring-closing and hydrogen evolution cascade processes.