Visible-Light Photocatalytic Functionalization of Isocyanides for the Synthesis of Secondary Amides and Ketene Aminals

Rolando Cannalire, Jussara Amato, Vincenzo Summa, Ettore Novellino, Gian Cesare Tron, Mariateresa Giustiniano

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

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.

Lingua originaleInglese
pagine (da-a)14077-14086
Numero di pagine10
RivistaJournal of Organic Chemistry
Volume85
Numero di pubblicazione21
DOI
Stato di pubblicazionePubblicato - 6 nov 2020

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