Fluoride-Catalyzed Cross-Coupling of Carbamoyl Fluorides and Alkynylsilanes

Org Lett. 2023 Oct 13;25(40):7369-7373. doi: 10.1021/acs.orglett.3c02871. Epub 2023 Sep 28.

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.