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Updated: Jul 15, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Fluoride-Catalyzed Cross-Coupling of Carbamoyl Fluorides and Alkynylsilanes
Dusty Cadwallader1, Dmytro Shevchuk1, Tristan R Tiburcio1
1Department of Chemistry, York University, Toronto, Ontario M3J 1P3, Canada.
Abstract:
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.
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