Visible-Light Mediated Carbamoylation of Nitrones under a Continuous Flow Regime.

Autor: Oliveira PHR; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, São Paulo 13565-905, Brazil., Tordato ÉA; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, São Paulo 13565-905, Brazil., Vélez JAC; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, São Paulo 13565-905, Brazil., Carneiro PS; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, São Paulo 13565-905, Brazil., Paixão MW; Centre of Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos - UFSCar, São Carlos, São Paulo 13565-905, Brazil.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 May 19; Vol. 88 (10), pp. 6407-6419. Date of Electronic Publication: 2022 Dec 28.
DOI: 10.1021/acs.joc.2c02266
Abstrakt: Herein, we report a rapid and scalable continuous-flow photocatalytic approach for the carbamoylation of nitrones. This protocol makes use of readily available 4-amido-1,4 dihydropyridines as carbamoyl radical precursors. The scope of this transformation exhibits high compatibility with complex structures containing amino acids, peptides, and glycosides. Importantly, the developed method allows a photocatalytic synthetic strategy in combination with flow conditions, maximizing the potential and efficiency for the synthesis of valuable α-( N -hydroxy)amino amides.
Databáze: MEDLINE