Dehydrogenative Photocyclization of 3-Styryl Indoles to Fused Indole Systems
JOURNAL OF ORGANIC CHEMISTRY, cilt.89, sa.23, ss.17447-17452, 2024 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 89 Sayı: 23
- 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
- Sayfa Sayıları: ss.17447-17452
- Ankara 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 6 pi-electrocyclic ring-closing and hydrogen evolution cascade processes.