A simple, mild, metal-free catalytic protocol is developed to convert amides to amines. This protocol uses a stable tetrabutylammonium difluorotriphenylsilicate in combination with silanes that generates a highly reactive hydrosilicate species, which enables the reduction of a broad range of amides to amines in moderate to good yields. The attractive features of this protocol include operational simplicity, safety, short reaction times, room temperature reaction, broad substrate scope, and amenable to scale up.
View Article and Find Full Text PDFHerein, we report for the first time a transition-metal-free frustrated Lewis pair (FLP) catalyzed CHF group migration from an oxygen atom to the neighboring nitrogen atom, which led to the synthesis of N-substituted benzimidazoles at room temperature with excellent yields, broad functional group tolerance, and a short reaction time. The oxygen-attached difluoromethane acted as a C1 source in the synthesis of N-substituted benzimidazoles in the presence of AlCl by cleaving one C-O bond and two C-F bonds, resulting in formation of two new C-N bonds.
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