(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.

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