Catalytic Room-Temperature C-N Coupling of Amides and Isocyanates by Using Mechanochemistry.

ABSTRACT

A mechanochemical route is developed for room-temperature and solvent-free derivatization of different types of amides into carbamoyl isatins (up to 96 % conversion or yield), benzamides (up to 81 % yield), and imides (up to 92 % yield). In solution, this copper-catalyzed coupling either does not take place or requires high temperatures at which it may also be competing with alternative thermal reactivity, highlighting the beneficial role of mechanochemistry for this reaction. Such behavior resembles the previously investigated coupling with sulfonamide substrates, suggesting that this type of C-N coupling is an example of a mechanochemically favored reaction, for which mechanochemistry appears to be a favored environment over solution.