Synthesis of Readily Modifiable Amides from Aldehydes via an Organocatalytic Approach Using a CTAB Surfactant

A simple and efficient organocatalytic method has been developed to access “readily modifiable” amides, including bench-stable N-acyl saccharin and various activated amides, from aldehydes by using CTAB-^tBuOOH. A wide range of aromatic and aliphatic acyl saccharin are obtained from their respective aldehydes with moderate to good yields. The approach can be similarly applied toward the formation of N-acyl imidazole, N-acyl benzimidazole, N-methoxy-N-methylamide (Weinreb amide), N-ethyl-N-phenylbenzamide, N-acyl morpholine, N-acyl valerolactam, and N-acyl caprolactam. These compounds are frequently applied as reagents in organic transformations, including acyl coupling, decarbonylative coupling, radical coupling, and coupling that is free from transition metals, enabling the synthesis of new C–C, C–N, C–O, C–S, C–P, and C–B bonds.