Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 10, Issue 2, Pages 375-381Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01711c
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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 allows the preparation of a broad family of N-substituted formamides in good yield. The heterogenized catalyst and reductant have been optimized to achieve high productivity.
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)(3)SiH 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.
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