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.
Visible-light photocatalytic functionalization of isocyanides for the synthesis of secondary amides and ketene aminals / Cannalire, R.; Amato, J.; Summa, V.; Novellino, E.; Tron, G. C.; Giustiniano, M.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 85:21(2020), pp. 14077-14086-14086. [10.1021/acs.joc.0c01946]
Visible-light photocatalytic functionalization of isocyanides for the synthesis of secondary amides and ketene aminals
Cannalire R.;Amato J.;Summa V.;Novellino E.;Giustiniano M.
2020
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.File | Dimensione | Formato | |
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