By the C-H activation methodology, aromatic C-H bonds can be easily substituted with different functional groups, without any previous functionalization of starting material. The introduction of a directing group (DG) allows regioselective metalation in the <i>ortho</i> position of the aromatic core. The application of hypervalent reagents opens new, shorter synthetic routes and facilitates mild reaction conditions. Due to their electrophilic character, high reactivity, easy preparation the +3 oxidation state organic iodonium salts are widespread in alkynylation and arylation reactions. Previously, our research group presented a simple and robust catalytic method for efficient and selective 2,2,2-trifluoroethylation reaction of aromatic compounds using the highly active trifluoroethyl(mesityl)iodonium salt.[1, 2] However, the application of alkenyliodonium salts is still underdeveloped. Here we present the first C-H activation reaction which utilize fluoralkenyliodonium salts as alkenylating agents for direct C-C coupling of aromatic amides, benzamides, ureas and ketones. The reaction conditions, scope and limitations have been investigated, and with this simple methodology we prepared more than 25 new <i>ortho</i>-fluoroalkenylated molecules.

Fluoroalkenyliodonium reagents in palladium-catalyzed ortho-C-H Activation of aromatic and heteroaromatic compounds

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.