Fluoride-Catalyzed Cross-Coupling of Carbamoyl Fluorides and Alkynylsilanes

We report the synthesis of alkynamides via the cross-coupling of carbamoyl fluorides and alkynylsilanes catalyzed by tetrabutylammonium fluoride (TBAF). In contrast to previously reported transformations of carbamoyl fluorides, C-F bond cleavage is achieved under exceptionally mild conditions (room temperature, low catalyst loadings, and short reaction times) without the need for strongly nucleophilic reagents and/or catalysts. This method offers distinct advantages over transition-metal-catalyzed approaches, such as tolerance to aryl halide moieties and complementary chemoselectivity.

Automated summary

This study presents a method for the synthesis of alkynamides through the cross-coupling of carbamoyl fluorides and alkynylsilanes catalyzed by tetrabutylammonium fluoride (TBAF). It achieves C-F bond cleavage under mild conditions without the need for strongly nucleophilic reagents and/or catalysts, offering advantages over transition-metal-catalyzed approaches in terms of tolerance to aryl halide moieties and complementary chemoselectivity.