(Z)-Selective Synthesis of Bromofluoroalkenes via the TMSCF2Br- Mediated Tandem Reaction with para-Quinone Methides

We report herein a tandem reaction of para-quinone methides with TMSCF2Br to construct bromofluoroalkenes in a Z-selective manner. While TMSCF2Br has been documented as the precursor of difluoro carbene, it exhibits another possibility in this transformation, a formal bromofluoro carbene surrogate. The alkenyl bromide unit of the products could directly engage in a variety of transformations.

Automated summary

Here, we report a tandem reaction of para-quinone methides with TMSCF2Br to synthesize bromofluoroalkenes in a Z-selective manner. TMSCF2Br, known as a difluorocarbene precursor, exhibits an alternative role as a formal bromofluorocarbene surrogate in this transformation. The resulting alkenyl bromide unit can undergo various transformations.