Published January 1, 2022
| Version v1
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Efficient Synthesis of 9-Aminophenanthrenes and Heterocyclic Analogues by Electrocyclization of Biaryl Keteniminium Salts
Creators
- 1. Syngenta Crop Protect AG, Crop Protect Res, Res Chem, Schaffhauserstr 101, CH-4332 Stein, Switzerland
- 2. Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey
Description
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.
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