Issue 2, 2023

Organocatalytic N-formylation of amines by CO2 in batch and continuous flow

Abstract

A continuous flow organocatalytic synthesis of formamides has been developed using amines and CO2 reaction partners in the presence of a silane reductant. The process is conducted under comparatively mild reaction conditions and allows the preparation of a broad family of N-substituted formamides in good yield. The heterogenized catalyst is a PS-supported superbase (DBU), while (MeO)3SiH proved to be the most efficient reductant. The reaction was first optimized in batch mode, giving access to fifteen different N-substituted formamide products. The optimized conditions were then used as input to develop a proof-of-concept continuous flow process based on the model substrate N-phenyl aniline thereby providing N-methyl-N-phenyl formamide as target with good productivity.

Graphical abstract: Organocatalytic N-formylation of amines by CO2 in batch and continuous flow

Supplementary files

Article information

Article type
Research Article
Submitted
27 Oct 2022
Accepted
18 Nov 2022
First published
21 Nov 2022

Org. Chem. Front., 2023,10, 375-381

Organocatalytic N-formylation of amines by CO2 in batch and continuous flow

N. Zanda, L. Primitivo, M. Chaudhari, A. W. Kleij and M. À. Pericàs, Org. Chem. Front., 2023, 10, 375 DOI: 10.1039/D2QO01711C

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