From amines to (form)amides: a simple and successful mechanochemical approach

• Federico Casti,
• Rita Mocci and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126

• mechanochemical conditions are presented. The two methodologies exhibit complementary features as they enable the derivatization of aliphatic and aromatic amines. Keywords: acetamides; formamides; mechanochemistry; N-formylation; p-tosylimidazole; Introduction The preparation of N-formylated and N-acetylated

• ). Switching to sodium sulfate as a grinding additive significantly enhanced the reaction performance (Table 1, entries 3 and 4). At this stage, we wondered, if using a more efficient dehydrating agent would be mandatory for the reaction to occur. Therefore, we turned our attention toward p-tosylimidazole (p

• -Tosylimidazole releases imidazole as a byproduct during the process. Therefore, we wondered whether imidazole could promote the formation of the target formamide 2. Imidazole, compared to p-tosylimidazole, is a cheaper reagent and makes the final purification process easier. As a matter of fact, by reacting 1.0

A trustworthy mechanochemical route to isocyanides

• Francesco Basoccu,
• Federico Cuccu,
• Federico Casti,
• Rita Mocci,
• Claudia Fattuoni and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 732–737, doi:10.3762/bjoc.18.73

• catalytic amount of NaHSO4 was necessary. Since isocyanides are sensitive to acids, this approach was ruled out a priori. Aware of these issues, we were discouraged from employing p-tosylimidazole as well, since it requires acid activation to be effective as a dehydrating agent. Accordingly, we moved our