Visible-Light Photocatalytic Functionalization of Isocyanides for the Synthesis of Secondary Amides and Ketene Aminals.
J Org Chem
; 85(21): 14077-14086, 2020 11 06.
Article
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| MEDLINE
| ID: mdl-33074674
ABSTRACT
A new visible light-induced photocatalytic protocol enabling the formation of secondary amides from electron-poor organic bromides and isocyanides was developed. In addition, the in situ interception of ketenimine intermediates with nitrogen nucleophiles such as amines, hydrazines, and TMSN3 afforded, in a one-pot two-step procedure, valuable scaffolds such as ketene aminals, pyrazolones, and tetrazoles. Mechanistic evidence confirmed a radical pathway where isocyanides acted as radical geminal acceptors generating key imidoyl radical species.
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Banco de datos:
MEDLINE
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En
Revista:
J Org Chem
Año:
2020
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Article
País de afiliación:
Italia