Efficient Synthesis of 9-Aminophenanthrenes and Heterocyclic Analogues by Electrocyclization of Biaryl Keteniminium Salts
Helvetica Chimica Acta, cilt.105, sa.11, 2022 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 105 Sayı: 11
- Basım Tarihi: 2022
- Doi Numarası: 10.1002/hlca.202200093
- Dergi Adı: Helvetica Chimica Acta
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, Veterinary Science Database, DIALNET
- Anahtar Kelimeler: density functional calculations, electrocyclic reactions, keteniminium salts, phenanthrene
- Boğaziçi Üniversitesi Adresli: Evet
Özet
We describe herein a high yielding and metal-free methodology to access 9-aminophenanthrene derivatives and heterocyclic analogues starting from biaryl acetamides. The conversion of the substrates to their corresponding keteniminium salts triggers a spontaneous electrocyclization occurring at room temperature within a few minutes. DFT Calculations and competition reactions were carried out to rationalize the observed reactivity and understand the relative kinetics compared to other known reactions involving keteniminium salts.