4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 10, Pages 6407-6419

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02266

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Here, a rapid and scalable continuous-flow photocatalytic approach for the carbamoylation of nitrones is reported. This method utilizes readily available 4-amido-1,4 dihydropyridines as carbamoyl radical precursors. The transformation shows high compatibility with complex structures containing amino acids, peptides, and glycosides. It also enables a photocatalytic synthetic strategy combined with flow conditions, maximizing the potential and efficiency for the synthesis of valuable alpha-(N-hydroxy)-amino amides.
Herein, we report a rapid and scalable continuous-flowphotocatalyticapproach for the carbamoylation of nitrones. This protocol makes useof readily available 4-amido-1,4 dihydropyridines as carbamoyl radicalprecursors. The scope of this transformation exhibits high compatibilitywith complex structures containing amino acids, peptides, and glycosides.Importantly, the developed method allows a photocatalytic syntheticstrategy in combination with flow conditions, maximizing the potentialand efficiency for the synthesis of valuable alpha-(N-hydroxy)-amino amides.

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