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21.1.6.5.1 Method 1: Catalytic Transamidation

DOI: 10.1055/sos-SD-021-00136

Li, W-R.Science of Synthesis, (200521209.

Primary amines and short-chain carboxamides (e.g., dimethylformamide) undergo direct transamidation, but the reaction times are long. However, aluminum trichloride activates N-unsubstituted (e.g., 128, R2=R3=H), N-substituted (e.g., 128, R2=H; R3H), and N,N-disubstituted amides (e.g., 128, R2H; R3H) toward transamidation (Scheme 29).[‌139‌] Primary amines (e.g., 129, R4=H) give higher yields of the product (e.g., 130) than secondary (e.g., 128, R4H) amines, whereas N-substituted amides give better yields than N-unsubstituted amides. The reactions of unactivated N,N-disubstituted amides (e.g., Scheme 29) with benzylamine give low yields, and the benzoyl group is less readily transferred than the acetyl group. Reaction does not occur in the case of aromatic or sterically hindered amines or of amides bearing bulky substituents.

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