N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light

Abstract

Herein, we describe the scalability and sustainability investigations toward the visible light-mediated amidation of aldehydes with N-chloro-N-sodio-carbamates. The practicality credentials of N-chloro-N-sodio-carbamates for their use in multigram scale amidation reactions are proven by scale-up productions and thermogravimetric analysis. The described amidation, which was previously hampered in sustainability perspectives by the use of alpha,alpha,alpha-trifluorotoluene solvent, is now improved through re-optimizations using ethyl acetate as an alternative green solvent. The generality of multigram scale amidations is demonstrated by the conversion of a selected list of aldehydes, in which the corresponding amides can be isolated in high purity without the need for special purification procedures.