Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation

Vinylboronates and alkylboronates are key components in variegated transformations in all facets of chemical science. The synthesis of vinylboronates and alkylboronates suffers from step-tedious and poor stereoselective procedures. We have developed a regulated radical difunctionalization strategy for the construction of fluorine-containing vinylboronates and alkylboronates with an integrated redox-active reagent IMDN-SO2RF. This bench-stable imidazolium sulfonate cationic salt offers a scalable and operational protocol for the fluoroalkylation-borylation of unsaturated hydrocarbons in a high regio- and stereoselective manner. The products can be further transformed into valuable fluorinated building blocks. The synthesis of vinylboronates and alkylboronates often suffers from step-tedious and poorly stereoselective procedures. Here, the authors report a bench-stable redox-active reagent for the radical difunctionalization of alkenes and alkynes affording fluorine-containing vinylboronates and alkylboronates.