Abstract
A mechanochemical synthesis of 1,2-disubstituted benzimidazoles from donor-acceptor cyclopropyl ketones and 1,2-diaminoarenes under metal-free and solventless conditions is reported. The reaction does not require inert conditions and is promoted by a stoichiometric amount of 1,1,1,3,3,3-hexafluoroisopropanol. This cascade reaction involves ring-opening, cyclization, and retro-Mannich reaction of cyclopropyl ketones with aryl 1,2-diamines. Compared to its solution-phase counterpart, this mechanochemical approach shows fast reactivity (24 vs 1.5 h). Mechanistic investigations by electrospray ionization mass spectrometry helped us to propose the reaction mechanism.
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