Journal
ORGANIC LETTERS
Volume 25, Issue 18, Pages 3271-3275Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c01007
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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.
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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